Name: 5700-60-7|1,2-Diphenylethane-1,2-diamine|98%
Brand: Ambeed
SKU: A542991
Price: 22.0 USD
Availability: InStock
Rating: 90 (28 reviews)

1
[ 5700-60-7 ]
N-((1R,6aR,9aS,9bR)-1-Hydroxy-2-oxo-2,4,5,6,6a,9,9a,9b-octahydro-1H-phenalen-1-yl)-isobutyramide [ No CAS ]
(3aS,11bR,11cS)-9,10-Diphenyl-3a,4,5,6,11b,11c-hexahydro-1H-8,11-diaza-benzo[de]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridinium p-toluenesulfonate In toluene at 90℃;

Reference： [1]Nicolaou; Zhong, Yong-Li; Baran, Phil S.; Sugita, Kazyuki [Angewandte Chemie - International Edition, 2001, vol. 40, # 11, p. 2145 - 2149]

2
[ 5700-60-7 ]
N-((1R,6aR,9aS,9bR)-1-Hydroxy-2-oxo-2,4,5,6,6a,9,9a,9b-octahydro-1H-phenalen-1-yl)-isobutyramide [ No CAS ]
(3aS,11bR,11cS)-9,10-Diphenyl-3a,4,5,6,9,10,11b,11c-octahydro-1H-8,11-diaza-benzo[de]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridinium p-toluenesulfonate In toluene at 90℃; for 12h;

Reference： [1]Nicolaou; Sugita; Baran; Zhong [Journal of the American Chemical Society, 2002, vol. 124, # 10, p. 2221 - 2232]

3
[ 84199-98-4 ]
[ 5700-60-7 ]
3-[(cis-4,5-diphenyl-4,5-dihydro1H-imidazol-2-yl)-2-ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 65℃; for 6h;	137.3 To a solution of the diamine 1 (159 mg 0.75 mmol) in toluene (5 mL) is added 2.0M trimethylaluminum in toluene (0.95 mL, 1.9 mmol), followed by 301 (124 mg, 0.75 mmol), and the solution is heated at 65° C. for 6 h. The reaction is cooled to RT and quenched by the addition of sat. sodium bicarbonate solution, followed by the addition of water and EtOAc. The organic layer is separated, and washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with dichloromethane:7M ammonia in MeOH (95:5) gives 104 mg of the product 302. 1H NMR (CDCl3) δ 8.62 (s, 1H), 8.52 (d, 1H), 7.67 (d, 1H), 7.28 (m, 1H), 7.05-7.00 (m, 6H), 6.8-6.7 (m, 4H), 5.27 (bs, 2H), 3.19 (t, 2H), 2.82 (t, 2H); MS: m/z 328 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 72

4
[ 28819-26-3 ]
[ 5700-60-7 ]
2-[(cis-4,5-diphenyl-4,5-dihydro1H-imidazol-2-yl)-2-ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 70℃; for 6h;	136.3 To a solution of 298 (165 mg, 1.0 mmol) in toluene (8 mL) is added the diamine 1 (212 mg 1.0 mmol) followed by 2.0M trimethylaluminum in toluene (1.2 mL, 1.2 mmol), and the solution is heated at 70° C. for 6 h. The reaction is cooled to RT and quenched by the addition of sat. sodium bicarbonate solution, followed by the addition of water and EtOAc. The organic layer is separated, and washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with dichloromethane:MeOH (9:1) gives 99 mg of the product 299. 1H NMR (CDCl3) δ 8.56 (d, 1H), 7.65 (t, 1H), 7.32 (d, 1H), 7.17 (m, 1H), 7.0-6.9 (m, 6H), 6.82-6.80 (m, 4H), 5.4-5.1 (bs, 2H), 3.34 (t, 2H), 3.00 (t, 2H); MS: m/z 328 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 72

5
[ 75-15-0 ]
[ 5700-60-7 ]
cis-4,5-diphenylimidazolidine-2-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 95℃;	14 Preparation 14; cis-4,5-Diphenyliniidazolidine-2-thione (25) A mixture of cis-1,2-diphenylethane-1,2-diamine (1) (50 g, 0.26 mol) and carbon disulfide (24 mL, 0.40 mol) in abs. EtOH (600 mL) is heated at 95° C. overnight. The reaction mixture is cooled to rt, concentrated in vacuo, and the residue suspended in cold 95% EtOH, and the insoluble material is filtered, to give 58.16 g of the product 25. 1H NMR (DMSO-d6) δ 8.73 (s, 2H), 7.10-6.95 (m, 6H), 6.95-6.85 (m, 2H), 5.31 (s, 2H); MS: m/z 255 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 27

6
[ 3598-14-9 ]
[ 5700-60-7 ]
2-[(phenoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum; In toluene; at 60℃; for 2h;	To a solution of the diamine 1 (212 mg, 1.0 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (1.0 mL, 2.0 mmol) followed by a solution of <strong>[3598-14-9]phenoxyacetonitrile</strong> (133 mg, 1.0 mmol) in toluene (1 mL). The solution is heated at 60 C. for 2 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (9:1) gives 119 mg of the product 383. 1H NMR (CDCl3) delta 7.37 (t, 2H), 7.1-6.9 (m, 9H), 6.88 (bs, 4H), 5.4 (bd, 2H), 5.01 (bs, 2H); MS: m/z 329 (M++1).

Reference： [1]Patent: US2005/26916,2005,A1 .Location in patent: Page/Page column 74

7
[ 5700-60-7 ]
[ 137988-23-9 ]
2-[(2-fluorophenoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 60℃; for 2h;	143.2 To a solution of the diamine 1 (212 mg, 1.0 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (1.0 mL, 2.0 mmol) followed by a solution of 384 (151 mg, 1.0 mmol) in toluene (1 mL). The solution is heated at 60° C. for 2 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloroinethane:MeOH (9:1) gives 59 mg of the product 385. 1H NMR (CDCl3) δ 7.40-7.25 (m, 1H), 7.24-7.11 (m, 3H), 7.00 (m, 6H), 6.88 (m, 4H), 5.37 (bs, 2H), 5.06 (bs, 2H); MS: m/z 347 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 74

8
[ 80056-43-5 ]
[ 5700-60-7 ]
1-[(cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)methyl]-1H-pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 70℃; for 6h;	162.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (4 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by a solution of 425 (90 mg, 0.5 mmol) in toluene (1 mL). The solution is heated at 70° C. for 6 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (1 mL) and EtOAc is added, and the mixture is filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (95:5) gives 23 mg of the product 426. 1H NMR (DMSO-d6) δ 10.97 (s, 2H), 7.84 (dd, 1H) 7.58 (dt, 1H), 7.15-7.0 (m, 10H), 6.60 (d, 1H), 6.39 (t, 1H), 5.79 (s, 2H), 5.25 (s, 2H); MS: m/z 330 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 81

9
[ 32122-09-1 ]
[ 5700-60-7 ]
2-[(benzyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum; In toluene; at 60℃; for 6h;	To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (3 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by 390 (100 mg, 0.5 mmol), and the solution is heated at 60 C. for 6 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.5 mL) and EtOAc is added, and the solution is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (92:8) gives 49 mg of the product 391. 1H NMR (CDCl3) delta 7.4-7.26 (m, 5H), 7.01 (m, 6H), 6.92 (m, 4H), 5.31 (bs, 2H), 4.70 (s, 2H), 4.48 (s, 2H); MS: m/z 343 (M+).

Reference： [1]Patent: US2005/26916,2005,A1 .Location in patent: Page/Page column 75

10
methyl 3-phenylpropanimidate hydrochloride [ No CAS ]
[ 5700-60-7 ]
2-phenethyl-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 80℃;	123 A mixture of cis-1,2-diphenylethane-1,2-diamine (1) (1.0 g, 4.7 mmol) and 3-phenyl-propionimidic acid methyl ester hydrochloride (242) (0.94 g, 4.7 mmol) in EtOH (10 mL) is heated at 80° C. overnight. The solvent is removed by rotary evaporation, and the residue dissolved in dichloromethane, and the solution washed with sodium carbonate, brine, then dried (MgSO4) and filtered. The filtrate is rotary evaporated to give 1.2 g of impure product 243.

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 64

11
[ 836656-33-8 ]
[ 5700-60-7 ]
2-[(3-fluorobenzyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 60℃; for 6h;	147.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (3 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by 392 (106 mg, 0.53 mmol), and the solution is heated at 60° C. for 6 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (94:6) followed by treatment with hydrogen chloride in Et2O gives 17 mg of the product 393. 1H NMR (CDCl3) δ 10.3 (bs, 2H), 7.37 (m, 1H), 7.26-7.0 (m, 9H), 6.88 (m, 4H), 5.68 (s, 2H), 5.17 (s, 2H), 4.73 (s, 2H)

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 76

12
[ 5700-60-7 ]
[ 192195-30-5 ]
2-(cyclohexylmethoxymethyl)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 65℃; for 4h;	159.2 To a solution of the diamine 1 (276 mg, 1.3 mmol) in toluene (4 mL) is added 2.0M trimethylaluminum in toluene (1.62 mL, 3.24 mmol) followed by a solution of 419 (260 mg, 1.3 mmol) in toluene (1 mL). The solution is heated at 65° C. for 4 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (3 mL) and EtOAc is added, and the mixture is filtered., dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with EtOAc:MeOH:heptane (65:5:30) gives 31 mg of the product 420. 1H NMR (DMSO-d6) δ 7.1 (bs, 1H), 7.0-6.9 (m, 10H), 5.22 (bs, 2H), 4.21 (s, 2H), 3.41-3.39 (d, 2H), 1.8-1.6 (m, 5H), 1.2-1.1 (m, 4H), 1.0-0.9 (m, 2H); LC/MS: 3.50 min, m/z 349 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 80

13
[ 836656-35-0 ]
[ 5700-60-7 ]
2-[(3-trifluoromethylbenzyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3-trifluoromethylbenzyloxy)acetic acid ethyl ester; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 60℃; for 6h; Stage #2: With hydrogenchloride In diethyl ether	148.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (3 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by 394 (131 mg, 0.53 mmol), and the solution is heated at 60° C. for 6 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (94:6) followed by treatment with hydrogen chloride in Et2O gives 14 mg of the product 395. 1H NMR (DMSO-d6) δ 10.90 (s, 2H), 7.85 (bs, 1H), 7.81-7.64 (m, 3H), 7.15-7.0 (m, 10H), 5.81 (s, 2H), 4.87 (s, 4H); MS: m/z 411 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 76

14
[ 836656-38-3 ]
[ 5700-60-7 ]
2-[(3-methylbenzyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3-methylbenzyloxy)acetic acid ethyl ester; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 60℃; for 6h; Stage #2: With hydrogenchloride In diethyl ether	149.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (3 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by 396 (194 mg, 0.53 mmol), and the solution is heated at 60° C. for 6 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (94:6) followed by treatment with hydrogen chloride in Et2O gives 40 mg of the product 397. 1H NMR (DMSO-d6) δ 10.91 (s, 2H), 7.34-6.99 (m, 14H), 5.79 (s, 2H), 4.79 (s, 2H). 4.72 (s, 2H), 2.34 (s, 3H); MS: m/z 357 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 76

15
[ 5700-60-7 ]
[ 54212-41-8 ]
2-[(3-methoxybenzyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-Diphenylethylenediamine; (3-methoxybenzyloxy)acetic acid ethyl ester With trimethylaluminum In toluene at 60℃; for 6h; Stage #2: With hydrogenchloride In diethyl ether	150.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (3 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by 398 (210 mg, 0.53 mmol), and the solution is heated at 60° C. for 6 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane:MeOH (94:6) followed by treatment with hydrogen chloride in Et2O gives 34 mg of the product 399. 1H NMR (DMSO-d6) δ 10.87 (s, 2H), 7.34 (t, 1H), 7.13-6.96 (m, 12H), 6.92 (m, 1H), 5.79 (s, 2H), 4.79 (s, 2H), 4.74 (s, 2H), 3.78 (s, 3H); MS: m/z 373 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 77

16
[ 5700-60-7 ]
[ 57941-73-8 ]
2-[(2-phenethyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylaluminum In toluene at 65℃; for 6h;	161.2 To a solution of the diamine 1 (318 mg, 1.5 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (2.25 mL, 4.5 mmol) followed by a solution of 423 (312 mg, 1.5 mmol) in toluene (2 mL). The solution is heated at 65° C. for 6 h, then cooled to RT. The reaction is quenched with sat. sodium bicarbonate solution (3 mL) and EtOAc: is added, and the mixture is filtered, and the filtrate is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with EtOAC:MeOH:heptane (70:10:20) gives 84 mg of the product 424. 1H NMR (DMSO-d6) δ 7.27 (d, 4H), 7.2-7.1 (m, 1H), 7.0-6.9 (m, 11H), 5.19 (bs, 2H), 4.24 (s, 2H), 3.78 (t, 2H), 2.89 (t, 2H); LC/MS: 3.33 min, m/z 357 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 81

17
[ CAS Unavailable ]
[ 817176-80-0 ]
[ 5700-60-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide ligand was reacted with Ru-complex in DMF at 100°C, treated with DPEN at room temp.;

Reference： [1]Xie, Jian-Hua; Wang, Li-Xin; Fu, Yu; Zhu, Shuo-Fei; Fan, Bao-Min; Duan, Hai-Feng; Zhou, Qi-Lin [Journal of the American Chemical Society, 2003, vol. 125, # 15, p. 4404 - 4405]

18
[ 37366-09-9 ]
[ 528521-89-3 ]
[ 5700-60-7 ]
[(((S)-Xyl-SDP)Ru(R,R-1,2-diphenylethylenediamine)Cl₂] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 4404 - 4405

19
[ 7605-25-6 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(phenylsulfanyl)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl phenylsulfenylacetate; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 80℃; for 2.5h; Stage #2: trifluoroacetic acid In water; acetonitrile	151.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (1.5 mL) is added 2.0M trimethylaluminum in toluene (0.65 mL, 1.3 mmol) followed by 400 (98 mg, 0.50 mmol), and the solution is heated at 80° C. for 2.5 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.6 mL) and EtOAc: dichloromethane is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; elution with acetonitrile:water/0.1% TFA gives 96 mg of the product 401. 1H NMR (CDCl3) δ 10.8 (bs, 2H), 7.60 (m, 2H), 7.45-7.3 (m, 3H), 7.05-6.9 (m, 6H), 6.58 (m, 4H), 5.52 (s, 2H), 4.50 (s, 2H); LC/MS: 3.24 min, m/z 345 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 77

20
[ 6436-90-4 ]
[ 5700-60-7 ]
[ 76-05-1 ]
[(cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)methyl]benzylamine ditrifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 2-(benzylamino)acetate; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 90℃; for 6.5h; Stage #2: trifluoroacetic acid In water; acetonitrile	160.2 To a solution of the diamine 1 (637 mg, 3.0 mmol) in toluene (11 mL) is added 2.0M trimethylaluminum in toluene (3.9 mL, 7.8 mmol) followed by a solution of 421 (580 mg, 3.0 mmol) in toluene (2 mL). The solution is heated at 90° C. for 6.5 h, then cooled to RT. The reaction is quenched with sat. sodium bicarbonate solution (4 mL) and EtOAc: dichloromethane is added, and the mixture is filtered, and the filtrate is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile/0.1% TFA:water/0.1% TFA (30:70-100:0) gives 166 mg of the product 422. 1H NMR (DMSO-d6) δ 10.61 (bs, 1H), 7.5-7.3 (m, 5H), 7.1-7.0 (m, 10H), 5.75 (s, 2H), 4.04 (s, 2H), 4.00 (s, 2H); LC/MS: 2.95 min, m/z 342 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 80-81

21
[ 5700-60-7 ]
[ 135290-20-9 ]
[ 76-05-1 ]
2-[(3-fluorophenoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-Diphenylethylenediamine; (3-Fluoro-phenoxy)-acetonitrile With trimethylaluminum In toluene at 60℃; for 2h; Stage #2: trifluoroacetic acid In water; acetonitrile	144.2 To a solution of the diamine 1 (212 mg, 1.0 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (1.0 mL, 2.0 mmol) followed by a solution 386 (151 mg, 1.0 mmol) in toluene (1 mL). The solution is heated at 60° C. for 2 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/1% TFA (30:70-100:0) gives 63 mg of the product 387. 1H NMR (CDCl3) δ 7.31 (q, 1H), 7.7.1-7.0 (m, 6H), 7.9-7.7 (m, 7H), 5.59 (s, 2H), 5.42 (s, 2H); MS: m/z 347 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 75

22
[ 6290-49-9 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(methoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl methoxyacetate; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 90℃; for 3h; Stage #2: trifluoroacetic acid In water; acetonitrile	153 Example 153; 2-[(Methoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Trifluoroacetate (404) To a solution of the diamine 1 (159 mg, 0.75 mmol) in toluene (2.5 mL) is added 2.0M trimethylaluminum in toluene (0.980 mL, 1.96 mmol) followed by methoxyacetic acid methyl ester (0.74 mL, 0.75 mmol), and the solution is heated at 90° C. for 3 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (1.5 mL) and EtOAc is added, and the mixture is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; elution with acetonitrile/0.1% TFA:water/0.1% TFA gives 63 mg of the product 404. 1H NMR (DMSO-d6) δ 10.85 (s, 1H), 7.1-7.0 (m, 10H), 5.80 (s, 2H), 4.71 (s, 2H), 3.51 (s, 3H); LC/MS: 2.80 min, m/z 267 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 78

23
[ 24115-20-6 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(4-fluorophenoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-fluorophenoxy)acetonitrile; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 60℃; for 2h; Stage #2: trifluoroacetic acid In water; acetonitrile	145.2 To a solution of the diamine 1 (212 mg, 1.0 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (1.0 mL, 2.0 mmol) followed by a solution 388 (151 mg, 1.0 mmol) in toluene (1 mL). The solution is heated at 60° C. for 2 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (2 mL) and EtOAc is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/1% TFA (30:70-100:0) gives 48 mg of the product 389. 1H NMR (CDCl3) δ 7.1-6.9 (m, 10H), 6.82 (m, 4H), 5.59 (bs, 2H), 5.42 (bs, 2H); MS: m/z 347 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 75

24
[ 5700-60-7 ]
[ 156002-64-1 ]
[ 76-05-1 ]
2-[(tetrahydropyran-4-yl)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-Diphenylethylenediamine; methyl 2-(tetrahydro-2H-pyran-4-yl)acetate With trimethylaluminum In toluene at 65℃; for 12h; Stage #2: trifluoroacetic acid In water; acetonitrile	138.3 To a solution of the diamine 1 (584 mg 2.75 mmol) in toluene (15 mL) is added 2.0M trimethylaluminum in toluene (3.44 mL, 6.88 mmol), followed by 304 (473 mg, 3.0 mmol), and the solution is heated at 65° C. for 12 h. The reaction is cooled to 20° C. and quenched by the addition of sat. sodium bicarbonate solution, and filtered. The filtrate is evaporated, and the residue is purified by reverse phase HPLC; gradient elution with acetonitrile/0.1% TFA:water/0.1% TFA (25:75-100:0) gives 178 mg of the product 305. 1H NMR (DMSO-d6) δ 10.72 (s, 2H), 7.2-7.1 (m, 6H), 7.05-7.0 (m, 4H), 5.80 (s, 2H), 3.95-3.90 (m, 2H), 3.36 (t, 2H), 2.74 (d, 2H), 2.15 (m, 1H), 1.75-1.70 (m, 2H), 1.45-1.30 (m, 2H); MS: m/z 321 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 73

25
[ 5700-60-7 ]
[ 2899-67-4 ]
[ 76-05-1 ]
2-[(benzylsulfanyl)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-Diphenylethylenediamine; ethyl (benzylthio)acetate With trimethylaluminum In toluene at 80℃; for 2.5h; Stage #2: trifluoroacetic acid In water; acetonitrile	152.2 Step 2; 2-[(Benzylsulfanyl)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Trifluoroacetate (403) To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (2 mL) is added 2.0M trimethylaluminum in toluene (0.65 mL, 1.3 mmol) followed by 402 (105 mg, 0.50 mmol), and the solution is heated at 80° C. for 2.5 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (0.6 mL) and EtOAc: dichloromethane is added, and the solution filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; elution with acetonitrile:water/0.1% TFA gives 96 mg of the product 403. 1H NMR (CDCl3) δ 10.8 (bs, 2H), 7.44-7.3 (m, 5H), 7.05 (m, 6H), 6.73 (m, 4H), 5.23 (s, 2H), 4.08 (s, 2H), 3.98 (s, 2H); LC/MS: 3.35 min, m/z 359 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 77-78

26
[ 5700-60-7 ]
[ 57941-70-5 ]
[ 76-05-1 ]
2-(cyclohexyloxy)methyl-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-Diphenylethylenediamine; ethyl 2-(cyclohexyloxy)acetate With trimethylaluminum In toluene at 60℃; for 2h; Stage #2: trifluoroacetic acid In water; acetonitrile	155.2 To a solution of the diamine 1 (212 mg, 1.0 mmol) in toluene (6 mL) is added 2.0M trimethylaluminum in toluene (1.0 mL, 2.0 mmol) followed by a solution of 407 (186 mg, 1.0 mmol) in toluene (1 mL). The solution is heated at 60° C. for 2 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (1.5 mL) and EtOAc is added, and the mixture is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/0.1% TFA (30:70-100:0) gives 54 mg of the product 408. 1H NMR (CDCl3) δ 7.10 (m, 6H), 6.89 (m, 4H), 5.67 (s, 2H), 4.96 (s, 2H), 3.53 (m, 1H), 1.99 (m, 2H), 1.76 (m, 2H), 1.57 (m, 1H), 1.2-1.05 (m, 5H); MS: m/z 335 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 78-79

27
[ 766539-48-4 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(tetrahydropyran-4-yloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 2-((tetrahydro-2H-pyran-4-yl)oxy)acetate; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 70℃; for 6h; Stage #2: trifluoroacetic acid In water; acetonitrile	156.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (4 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by a solution of 409 (95 mg, 0.5 mmol) in toluene (1 mL). The solution is heated at 70° C. for 6 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (1 mL) and EtOAc is added, and the mixture is filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/0.1% TFA (30:70-100:0) gives 109 mg of the product 410. 1H NMR (DMSO-d6) δ 10.76 (s, 2H), 7.15-7.00 (m, 10H), 5.80 (s, 2H), 4.80 (s, 2H), 3.9-3.75 (m, 3H), 3.39 (dt, 2H), 1.96 (m, 2H), 1.56 (m, 2H); MS: m/z 337 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 79

28
[ 836656-54-3 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(cycloheptyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cycloheptyloxyacetic acid ethyl ester; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 70℃; for 6h; Stage #2: trifluoroacetic acid In water; acetonitrile	157.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (4 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by a solution of 411 (100 mg, 0.5 mmol) in toluene (1 mL). The solution is heated at 70° C. for 6 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (1 mL) and EtOAc is added, and the mixture is filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/0.1% TFA (30:70-100:0) gives 58 mg of the product 412. 1H NMR (DMSO-d6) δ 10.70 (s, 2H), 7.15-7.00 (m, 10H), 5.79 (s, 2H), 4.70 (s, 2H), 3.73 (m, 1H), 1.94 (m, 2H), 1.95 (m, 2H), 1.73-1.6 (m, 4H), 1.6-1.5 (m, 4H), 1.5-1.3 (m, 2H); MS: m/z 349 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 79

29
[ 836656-58-7 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(cyclooctyloxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclooctyloxyacetic acid ethyl ester; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 70℃; for 6h; Stage #2: trifluoroacetic acid In water; acetonitrile	158.2 To a solution of the diamine 1 (106 mg, 0.5 mmol) in toluene (4 mL) is added 2.0M trimethylaluminum in toluene (0.6 mL, 1.2 mmol) followed by a solution of 413 (107 mg, 0.5 mmol) in toluene (1 mL). The solution is heated at 70° C. for 6 h, then cooled to RT. The reaction mixture is quenched with sat. sodium bicarbonate solution (1 mL) and EtOAc is added, and the mixture is filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; gradient elution with acetonitrile:water/0.1% TFA (30:70-100:0) gives 53 mg of the product 414. 1H NMR (CDCl3) δ 7.15-7.0 (m, 6H), 6.88 (m, 4H), 5.67 (s, 2H), 4.93 (s, 2H), 3.71 (m, m, 1H), 1.95-1.8 (m, 2H), 1.8-1.6 (m, 4H), 1.6-1.4 (m, 8H); MS: m/z 363 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 80

30
[ 42415-64-5 ]
[ 5700-60-7 ]
[ 76-05-1 ]
2-[(isopropoxy)methyl]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl isopropoxyacetate; 1,2-Diphenylethylenediamine With trimethylaluminum In toluene at 90℃; for 3h; Stage #2: trifluoroacetic acid In water; acetonitrile	154.2 To a solution of the diamine 1 (159 mg, 0.75 mmol) in toluene (2.5 mL) is added 2.0M trimethylaluminum in toluene (0.980 mL, 1.96 mmol) followed by 405 (110 mg, 0.75 mmol), and the solution is heated at 90° C. for 3 h, then cooled to rt. The reaction mixture is quenched with sat. sodium bicarbonate solution (1.5 mL) and EtOAc is added, and the mixture is dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on reversed phase silica gel; elution with acetonitrile/0.1% TFA:water/0.1% TFA gives 56 mg of the product 406. 1H NMR (DMSO-d6) δ 10.73 (s, 1H), 7.2-7.0 (m, 10H), 5.79 (s, 2H), 4.72 (s, 2H), 3.86 (m, 1H), 1.25 (s, 3H), 1.23 (s, 3H); LC/MS: 3.05 min, m/z 295 (M++1).

Reference： [1]Current Patent Assignee: SANOFI - US2005/26916, 2005, A1 Location in patent: Page/Page column 78

31
[ 512822-34-3 ]
[ 5700-60-7 ]
tert-butyl 4',5'-diphenyl-1',3',4',5'-tetrahydrospiro[3-azabicyclo[3.3.1]nonane-9,2'-imidazole]-3-carboxylate [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 1018 - 1023

32
[ 5700-60-7 ]
[ 81879-64-3 ]
3-benzyl-4',5'-diphenyl-1',3',4',5'-tetrahydrospiro[3-azabicyclo[3.3.1]nonane-9,2'-imidazole] [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 1018 - 1023

33
[ 5700-60-7 ]
[ 1173893-17-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen sulfide; magnesium sulfate In ethanol; ethyl acetate	S.1.2 Step 2: Step 2: Synthesis of 5-(3-fluorophenyl)-2,3-diphenylpyrazine (abbreviation: Hdppr-3FP) To a reaction container for irradiation of a microwave were placed 0.20 g (1.0 mmol) of 1-(3-fluorophenyl)-2-(methylsulfinyl)ethanone, which is an intermediate and was obtained in the above Step 1, 0.21 g (1.0 mmol) of meso-1,2-diphenylethylenediamine, and 0.067 g (2.1 mmol) of sulfur (crystal), and 1 mL of ethanol was added to the mixture. This mixture was irradiated with a microwave (2.45 GHz, 50 to 100 W (change depending on reaction temperature and pressure)) for 60 minutes to be reacted. Note that the reaction temperature was set to be 70 to 75° C., and the reaction pressure was set to be 40 to 45 psi (28104 Pa to 31104 Pa). After the reaction, to 100 mL of 1 M dilute hydrochloric acid was added the reaction mixture. Ethyl acetate was added to this reaction mixture to extract an organic layer, and the organic layer was separated. The separated organic layer was washed with 1 M dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution in this order. After washing, magnesium sulfate was added to the organic layer to dry the organic layer. After drying, this mixture was subjected to suction filtration to remove magnesium sulfate, so that a filtrate was obtained.
	With hydrogenchloride; hydrogen sulfide; magnesium sulfate In dimethyl sulfoxide; ethyl acetate	S.3.2 Step 2: Step 2: Synthesis of 5-(3-fluorophenyl)-2,3-diphenylpyrazine (abbreviation: Hdppr-3FP) To a reaction container for irradiation of a microwave were placed 0.20 g (1.0 mmol) of 1-(3-fluorophenyl)-2-(methylsulfinyl)ethanone, which is an intermediate and was obtained in the above Step 1, 0.21 g (1.0 mmol) of meso-1,2-diphenylethylenediamine, and 0.067 g (2.1 mmol) of sulfur (crystal), and 1 mL of dimethylsulfoxide (abbreviation: DMSO) was added to the mixture. This mixture was irradiated with a microwave (2.45 GHz, 90 to 100 W (change depending on reaction temperature and pressure)) for 10 minutes to be reacted. Note that the reaction temperature was set to be 90 to 100° C., and the reaction pressure was set to be 50 to 55 psi (34104 Pa to 38104 Pa). After the reaction, to 100 mL of 1 M dilute hydrochloric acid was added the reaction mixture. Ethyl acetate was added to this reaction mixture to extract an organic layer, and the organic layer was separated. The separated organic layer was washed with 1 M dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution in this order. After washing, magnesium sulfate was added to the organic layer to dry the organic layer. After drying, this mixture was subjected to suction filtration to remove magnesium sulfate, so that a filtrate was obtained.
	With hydrogen sulfide In 2-ethoxy-ethanol; ethyl acetate	S.4.2 Step 2: Step 2: Synthesis of 5-(3-fluorophenyl)-2,3-diphenylpyrazine (abbreviation: Hdppr-3FP) To a reaction container for irradiation of a microwave were placed 0.21 g (1.0 mmol) of 1-(3-fluorophenyl)-2-methanesulfinylethanone, which is an intermediate and was obtained in the above Step 1, 0.20 g (1.0 mmol) of meso-1,2-diphenylethylenediamine, and 0.067 g (2.1 mmol) of sulfur (crystal), and 1 mL of 2-ethoxyethanol was added to the mixture. This mixture was irradiated with a microwave (2.45 GHz, 50 W) for 10 minutes to be reacted. Note that the reaction temperature was set to be 60° C., and the reaction pressure was set to be 10 to 15 psi (6.9104 Pa to 10104 Pa). After the reaction, the reaction mixture was concentrated, and ethyl acetate was added to this reaction mixture. This mixture was washed with 1 M dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution in this order.

In ethanol

S.2.2 Step 2: Step 2: Synthesis of 5-(3-fluorophenyl)-2,3-diphenylpyrazine (abbreviation: Hdppr-3FP) Next, to a three-necked flask were placed 2.5 g of 1-(3-fluorophenyl)-2-(methylsulfinyl)ethanone, which is an intermediate and was obtained in the above Step 1 and 2.7 g of meso-1,2-diphenylethylenediamine, and 65 mL of ethanol was added to the mixture. This mixed solution was stirred while being heated at 80° C. under a stream of nitrogen. This mixed solution was taken out to reaction containers in increments of 10 mL.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US7993494, 2011, B2
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US7993494, 2011, B2
[3]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US7993494, 2011, B2
[4]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US7993494, 2011, B2

34
[ 5700-60-7 ]
[ 90-02-8 ]
N,N'-bis(salicylidene)-1,2-diphenylethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethanol at 25℃; for 1h;	Synthesis of dPhS meso-1,2-Diphenyl-ethylenediamine (4.0 g, 18.80 mol) was added into a round-bottom flask containing 50 mL ethanol. To this solution, salicylaldehyde (3.70 mL, 37.60 mmol) was added and the mixture was stirred at 25 °C for 1 h, resulting in formation of a yellow precipitate. The reaction mixture was filtered, and the product was washed with ethanol to obtain dPhS as a yellow crystalline solid. Yield was 7.58 g (17.93 mmol), 95%, yellow crystalline solid. 1H-NMR (d6-DMSO, 360 MHz,δ): 5.06 (s, 2H, -CH-CH-), 6.85 (d,J= 8.0 Hz, 4H, CHarom), 7.20-7.32 (m, 12H, CHarom), 8.43 (s, 2H, CH=N-), 13.17 (s, 2H, -OH). 13C{1H} NMR (d6-DMSO, 90 MHz,δ): 166.17, 160.11, 139.93, 132.53, 131.75, 128.23, 127.86, 127.44, 118.69, 118.50, 116.34, 77.70.
93%	In ethanol for 1.5h; Reflux;

Reference： [1]Bunda, Szilvia; Joó, Ferenc; Kathó, Ágnes; Udvardy, Antal; Voronova, Krisztina [Molecules, 2020, vol. 25, # 17]
[2]Location in patent: experimental part Li, Lijun; Tian, Chao; Wang, Cheng; Wang, Guangyuan; Wang, Lianzeng; Du, Jianlong [E-Journal of Chemistry, 2012, vol. 9, # 3, p. 1422 - 1430]

35
[ 5700-60-7 ]
[ 5804-85-3 ]
C₁₅H₁₄AlN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In toluene at 20℃; for 6h; Inert atmosphere;	3 Example 3 For the Synthesis of Aluminum Complexes General procedure: The Strecker cyanide sources derived from hydroxy carboxylic acids, amino acids, diamines, amino alcohols and diols can be prepared by following general procedure. Into a dried and nitrogen flushed round-bottom flask, the corresponding diamine or diol (0.1 g, 0.34 mmol, and toulene (3.0 mL) were loaded. The resulting mixture was protected under nitrogen and diethyl aluminum cyanide (1 M, 0.34 mmol) was added dropwise. The reaction was stirred at room temperature for 6 h and monitored by 1H NMR. After the reaction was completed, the solvent was dried off completely to get the product. Aluminum complex with 1,2-diphenyl amine [Formula (IV)], (a), X=Ph, Y═H, W═CN] white solid (yield 82%); 1H NMR (300 MHz, CDCl3) δ 7.20-7.02 (m, 10H), 3.71 (s, 2H), 2.60-2.40 (m, 2H), 0.98 (dd, J1=6.0 Hz, J2=12.6 Hz 12H). Aluminum complex with S-BINOL [Formula (III), (a), X═H, W═CN] off white solid (yield 86%); 1H NMR (300 MHz, CDCl3) δ 8.06-7.82 (dd, J1=7.5 Hz, J2=12.0 Hz, 2H), 7.41-7.17 (m, 10H). Aluminium complex with pinacol [Formula (III-2), (f)] off white solid (yield 87%); 1H NMR (300 MHz, CDCl3) δ 1.38 (s, 12H). 1,3-Propanediol-derived aluminium complex with pinacol [Formula (III), (m)] (yield 87%) 1H NMR 6 (300 MHz, CDCl3): 3.90-3.84 (m, 4H), 1.90 (t, J=6.0 Hz, 2H), 1.83 (t, J=4.5 Hz, 2H).

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY; TEXAS TECH UNIVERSITY SYSTEM; NOWA PHARMACEUTICALS - US2013/137889, 2013, A1 Location in patent: Paragraph 0072

36
[ 5700-60-7 ]
[ 134-81-6 ]
[ 642-04-6 ]

Yield	Reaction Conditions	Operation in experiment
46.9%	With acetic acid for 4h; Reflux;	1 synthetic method references (J.A. Katzenellenbogen, the et al., Bioorg. Med.Chem., 2003, 11, 629): 50 ml round bottom flask, add 1, 2 - diphenyl diamine 212 mg (1 mmol), two benzil 210 mg (1 mmol) and 2 ml acetic acid. The reaction in the reflux in acetic acid 4 h, cooling and filtering, the filter residue in the re-crystallization in acetic acid, to obtain white needle crystal, yield: 46.9%.
	With acetic acid for 4h; Reflux;

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN104447582, 2017, B Location in patent: Paragraph 0070-0075
[2]Chen, Ming; Li, Lingzhi; Nie, Han; Tong, Jiaqi; Yan, Lulin; Xu, Bin; Sun, Jing Zhi; Tian, Wenjing; Zhao, Zujin; Qin, Anjun; Tang, Ben Zhong [Chemical Science, 2015, vol. 6, # 3, p. 1932 - 1937]

37
[ 39229-12-4 ]
[ 5700-60-7 ]
2-(4-bromophenyl)-3,5,6-triphenylpyrazine [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 2901 - 2908

38
[ 23873-81-6 ]
[ 5700-60-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyrographite; hydrazine hydrate; In methanol; at 58 - 62℃;Inert atmosphere;	1,2-diphenylethanedione dioxime (48 g, 0.20 mol) and 260 ml of methanol were placed in a 500 ml four-necked flask equipped with a condenser, and the whole was dissolved by stirring. Then, 2 g of activated carbon (120 mesh) 0.5 g Raney nickel, heated to 60 C,80% hydrazine hydrate (28.75g,0.46mol) was slowly added dropwise, keeping the reaction temperature at 58C -62C The reaction process was controlled by nitrogen gas, and the dropping speed was controlled to be too fast for nitrogen gas release. Chromatography tracks the progress of the reaction. When the starting 1,2-diphenylethanedione dioxime disappears, the reaction is terminated, the mixture is cooled, Raney nickel and activated carbon are filtered, covered with a small amount of water and the filtrate was distilled to recover the methanol. The residue was dissolved in 200 ml of petroleum ether, and the product was dissolved for 24 hours. The product was filtered to obtain (±) 1,1-diphenylethylenediamine in a yield of 98%. Chemical purity 99. 57% ?

Reference： [1]Patent: CN105218380,2016,A .Location in patent: Paragraph 0031-0034
[2]Molecules,2018,vol. 23

39
[ 111-71-7 ]
[ 5700-60-7 ]
3-pentyl-5,6-diphenylpiperazin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: heptanal With N-chloro-succinimide; rac-Pro-OH In dichloromethane at 20℃; for 16h; Stage #2: With sodium chlorite; sodium dihydrogenphosphate In water; <i>tert</i>-butyl alcohol for 1.5h; Stage #3: 1,2-Diphenylethylenediamine In acetonitrile at 100℃; for 2h; Microwave irradiation;

Reference： [1]Kaplaneris, Nikolaos; Spyropoulos, Constantinos; Kokotou, Maroula G.; Kokotos, Christoforos G. [Organic Letters, 2016, vol. 18, # 22, p. 5800 - 5803]

40
[ 5700-60-7 ]
[ 491-67-8 ]
2,3,7-triphenyl-10-hydroxy-1,2,3,4-tetrahydro-9H-pyrano[2,3-g]quinoxaline-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol at 78℃; for 20h;	1 1.06 g of 1,2-diphenylethylenediamine and 1.35 g of baicalein were added to a three-necked flask containing 20 mL of ethanol solution Stirring, the system temperature to 78 ° C, the reaction of 20 hours, taking advantage of heat, the filtrate directly recrystallization, the red crystal 1.502g, The yield was 62%. The product was examined by nuclear magnetic resonance and single crystal X-ray diffractometer. As shown in the figure, Fig. 1 is a 1 H NMR (DMSO) Each peak is homologous and there is no obvious impurity peak in the figure, indicating that the compound obtained is pure phase. Figure 2 for the product of the three-dimensional structure projection Figure, can be intuitive to get the product of the three-dimensional structure. In conjunction with Figure 1, it was confirmed that the high purity target product 2,3,7-triphenyl- 10-hydroxy-1,2,3,4-tetrahydro-9H-pyrano [2,3-g] quinoxaline-9-one

Reference： [1]Current Patent Assignee: LIAONING UNIVERSITY - CN106083869, 2016, A Location in patent: Paragraph 0019-0020

41
[ 5700-60-7 ]
C₉H₁₄O₂ [ No CAS ]
6,6-dimethyl-2,3-diphenyl-2,3,5,6,7,8-hexahydro-5,7-methanoquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In toluene at 120℃; for 5h; Inert atmosphere; Dean-Stark;	6,6-dimethyl-2,3-diphenyl-2,3,5,6,7,8- hexahydro-5,7-methanoquinoxaline (7) A mixture of 3-hydroxynopinone 5 (50 mg, 0.324 mmol)and 1,2-diphenylethylene amine (34.5 mg, 0.162 mmol) in toluene (4 mL) was stirred under reflux using dean stark apparatus for about 5 hours. The progress of the reaction was monitored by TLC. After completion, the mixture was extracted with dichloromethane (3x20 mL). The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography(10% ethyl acetate/hexane) to yield 7 as a colorless solid (62.0% yield). 1H NMR (400 MHz, CDCl3): δ 7.20(m, 4H), 7.01 (m, 6H), 4.50 (d, J = 13.2 Hz, 1H), 4.37 (d,J = 13.0 Hz, 1H), 2.98 (t, J = 5.7 Hz,, 1H), 2.83 (m, 2H),2.79 (m, 1H), 2.34 (s, 1H), 1.52 (d, J = 11 HZ, 1H), 1.48 (s,3H), 0.97 (s, 3H); 13C NMR (100 MHz,CDCl3+CCl4): δ163.0, 159.3, 141.8, 141.5, 128.1, 128.0, 127.1, 66.1, 65.0,50.9, 39.3, 36.3, 32.5, 26.0, 21.8; IR (neat): υ 3076, 2960,2874, 1654, 1453, 1095, 853 cm-1; HRMS calcd forC23H24N2[M+]: 329.2018, found: 329.2061.

Reference： [1]Reddy, Boggu Jagan Mohan; Konreddy, Ananda Kumar; Rani, Grandhe Usha; Rambabu; Raju, N. Prudhvi; Anjibabu; Gajare, Anil; Reddy, Basireddy Venkata Subba; Sreenivasulu, Reddymasu [Letters in Organic Chemistry, 2017, vol. 14, # 3, p. 218 - 225]

42
[ 5700-60-7 ]
[ 617-36-7 ]
[ 39213-73-5 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With pyridine; for 12h;Reflux;	1,2-Diphenylethylenediamine (30 g, 141 mmol)Then, <strong>[617-36-7]ethyl oxamate</strong> (24.82 g, 212 mmol) was added to 200 mL of pyridine and refluxed for 12 hours.When the reaction is complete, the solution is allowed to cool and poured into excess ethyl alcohol / DIW mixed solution to form a precipitate. The precipitate was filtered off and recrystallized in ethyl alcohol to obtain Compound 18 (34.8 g, Y = 93.5%).

Reference： [1]Patent: KR2017/50048,2017,A .Location in patent: Paragraph 0247-0251

43
[ 100-52-7 ]
[ 5700-60-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris(bipyridine)ruthenium(II) dichloride hexahydrate; ammonia; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate) In methanol; acetonitrile at 0 - 25℃; for 15h; Sealed tube; Inert atmosphere; Irradiation; chemoselective reaction;
	Multi-step reaction with 2 steps 1: ammonium acetate / 3 h / Reflux 2: sulfuric acid / 1 h / Reflux

Reference： [1]Rong, Jiawei; Seeberger, Peter H.; Gilmore, Kerry [Organic Letters, 2018, vol. 20, # 13, p. 4081 - 4085]
[2]Arish, D.; Bhuvanesh, N.; Kumaresan, S.; Shiju, C. [Polyhedron, 2021, vol. 205]

44
[ 5700-60-7 ]
[ 1885-14-9 ]
C₂₈H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 0 - 20℃;	Example: 10 mmol of 1,2-diphenylethylenediamine was dissolved in a 50 mL dichloromethane flask, thetemperature of the mixture was controlled to be about 0 ° C, and pyridine was added dropwise to the reactionmixture, and the amount of pyridine was only 10 mol% of the substrate, followed by 20 mmol of phenylchloroformate was added dropwise to the reaction system, and after the dropwise addition, the temperaturewas raised to room temperature and stirred for 4-6 hours. TLC was used to track the progress of theexperiment. After the reaction was completed, 20 mL of 1 mol of L -1 hydrochloric acid was added , and theorganic phase was washed with 20 mL of 1 mol of L -1 hydrochloric acid, 20 mL of saturated brine, dried overanhydrous sodium sulfate, and the solvent was dried to obtain purity. The higher white intermediate productdid not require further purification with a yield of 90% and a purity of greater than 95%.

Reference： [1]Current Patent Assignee: SHAOXING UNIVERSITY - CN109293530, 2019, A Location in patent: Paragraph 0022-0026

45
[ 5700-60-7 ]
[ 134-81-6 ]
[ 857223-04-2 ]

Yield	Reaction Conditions	Operation in experiment
80.4%	With perlite supported bismuth chloride In ethanol at 20℃; for 0.75h;	General procedure forsynthesis ofquinoxalines General procedure: The mixture of various diamines (0.001 mol) and benzil (0.001 mol) in etha-nol (3-5 mL) with 0.1 g of catalyst was stirred at room temperature for about 5 to 50 min. The reaction progress was examined using thin layer chromatography (TLC) with hexane as solvent. At the point of completion, the insoluble catalyst was filtered, and the product was separated by adding ethyl acetate. The crude product obtained by evaporating the solvent was purified by recrystallization using ethanol as solvent. The structure of the compounds was confirmed by FT-IR, 1 H NMR & 13 C NMR spectral analysis.

Reference： [1]Brindha, Kannan; Amutha, Parasuraman; Krishnakumar, Balu; do Nascimento Sobral, Abílio José Fraga [Research on Chemical Intermediates, 2019, vol. 45, # 9, p. 4367 - 4381]

46
[ 5700-60-7 ]
[ 90-02-8 ]
[ 3046-82-0 ]
C₁₇₃H₁₄₄N₁₂O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.23 g	In toluene at 20℃; for 72h;	Synthesis of Oligo-Salen-B 5,5’-methylenebis-2-hydroxybenzaldehyde (0.150 g, 0.58 mmol), 2-hydroxy-benzhaldehyde (62 μL, 0.58 mmol), andmeso-1,2-diphenylethylenediamine (0.192 g, 0.87 mmol) were stirred in anhydrous toluene (22 mL) at room temperature for 72 h. Then the solvent was removed under reduced pressure, thus leading to the Oligo-Salen-B (0.230 g) as pale yellow crystals, then washed with hexane:1H NMR (500MHz, CDCl3) δ 13.1-12.8 (bs, 2H, OH), 8.1-7.9 (m, 2H, CH=N), 7.4-6.7 (m, 18H, ArH), 4.8-4.6 (bs, 2H, Ar-CH-N), 3.7 (bs, 2H, Ar-CH2-Ar) ppm. Anal. Calcd. for C174H156N12O12: Found C, 80.14; H, 6.00; N, 6.39.

Reference： [1]Puglisi, Roberta; Mineo, Placido G.; Pappalardo, Andrea; Gulino, Antonino; Sfrazzetto, Giuseppe Trusso [Molecules, 2019, vol. 24, # 11]

47
[ 5700-60-7 ]
[ 90-02-8 ]
[ 3046-82-0 ]
C₁₁₅H₉₆N₈O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 mg	In toluene at 20℃; for 72h;	Synthesis of Oligo-Salen-C 5,5’-methylenebis-2-hydroxybenzaldehyde (39 mg, 0.15 mmol), 2-hydroxy-benzhaldehyde (32 μL, 0.30 mmol), andmeso-1,2-diphenylethylenediamine (66 mg, 0.30 mmol) were stirred in anhydrous toluene (22 mL) at room temperature for 72 h. Then the solvent was removed under reduced pressure, thus leading to the Oligo-Salen-C (40 mg) as yellow crystals, then washed with hexane:1H NMR (500MHz, CDCl3) δ 13.1-12.8 (bs, 2H, OH), 8.1-7.9 (m, 2H, CH=N), 7.4-6.7 (m, 18H, ArH), 4.8-4.6 (bs, 2H, Ar-CH-N), 3.7 (bs, 2H, Ar-CH2-Ar) ppm. Anal. Calcd. for C116H104N8O8: Found C, 80.11; H, 6.02; N, 6.44.

Reference： [1]Puglisi, Roberta; Mineo, Placido G.; Pappalardo, Andrea; Gulino, Antonino; Sfrazzetto, Giuseppe Trusso [Molecules, 2019, vol. 24, # 11]

48
[ 5700-60-7 ]
[ 4637-24-5 ]
4,5-diphenyl-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	at 70℃; for 8h;	1 Embodiment 1 50g compounds 500 ml (01) and 30.9g (1 . 1eq) N were added to the unitunitarily single-mouth flask. Methyl dimethyl formamide dimethyl acetal (DMF-DMA), stirred, stirred, stirred, cooled down to room temperature, filtered, and filtered and washed times in a vacuum drying, unitz cyclohexane, filtered, filtered, filtered, and evaporated to dryness in vacuo; and the residue was filtered and evaporated to dryness under vacuum. N- 160 ml 8h 50 °C - 60 °C 6h 80 °C 40 °C 50 ml 70 °C 1 The milk white product 49.7g, represented by the formula (02), was unitless , unitless, 95% and unitarily 99.4%.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN110066233, 2019, A Location in patent: Paragraph 0046

49
[ 358-23-6 ]
[ 5700-60-7 ]
[ 189114-80-5 ]
C₁₅H₁₅F₃N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 10℃; for 0.5h; Inert atmosphere;	8 Example 8 comparative examples 2g compound (01), was added to the reaction flask. After 15 ml the addition 1.43g (1 . 46eq) N, N - diethylaminoisopropylamine, N-diethylaminoisopropylamine was 10 ml dissolved 2.96g (1 . 26eq) trifluoromethanesulfonic anhydride in a constant pressure dropping funnel, and the mixture 30 min was stirred 10 °C to slowly dropwise add a trifluoromethanesulfonic anhydride solution, then the reaction solution, and the compound (I) unitarily 27.8% were detected. unitunitant methylene chloride was added dropwise to the reaction 1h, and then the reaction mixture was stirred overnight. Bi-substituted impurities are unitless 33.6%.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN110066233, 2019, A Location in patent: Paragraph 0072-0074

50
[ 40396-54-1 ]
[ 5700-60-7 ]
2-(3-bromophenyl)-3,5,6-triphenylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With acetic acid for 4h; Reflux;
66%	With acetic acid at 75℃; for 24h;	Ba Ba) 2-(3-bromophenyl)-3,5,6-triphenylpyrazine A flask was charged with 1-(3-bromophenyl)-2-phenylethane-1,2-dione (36.6 g, 126.5 mmol), 1,2-diphenylethane-1,2-diamine (38.7 g, 182.1 mmol), and acetic acid (320) mL. The mixture was heated to 75° C. for 24 h. Subsequently, the reaction mixture was concentrated under reduced pressure to approx. 100 mL and then carefully poured into sat. aq. K2CO3 (700 mL). After extraction with dichloromethane three times, the combined organic phases were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica, n-hexane/dichloromethane 8:2) and trituration with n-hexane to afford 38.8 g (66%) of a yellow solid after drying.
	With acetic acid at 75℃; for 24h;	A flask was charged with l-(3-bromophenyl)-2-phenylethane-l,2-dione (36.6 g, 126.5 mmol), 1,2-diphenylethane- 1,2-diamine (38.7 g, 182.1 mmol), and acetic acid (320) mL. The mixture was heated to 75 °C for 24 h. Subsequently, the reaction mixture was concentrated under reduced pressure to approx. 100 mL and then carefully poured into sat. aq. K2C03 (700 mL). After extraction with dichloromethane three times, the combined organic phases were washed with brine, dried over MgS04, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica, n-hexane/dichloromethane 8:2) and trituration with n-hexane to afford 38.8 g (66%) of 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)phenyl)pyrazineafter drying .

Reference： [1]Chen, Ming; Liu, Junkai; Liu, Feng; Nie, Han; Zeng, Jiajie; Lin, Gengwei; Qin, Anjun; Tu, Mei; He, Zikai; Sung, Herman H. Y.; Williams, Ian D.; Lam, Jacky W. Y.; Tang, Ben Zhong [Advanced Functional Materials, 2019, vol. 29, # 37]
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2021/198215, 2021, A1 Location in patent: Paragraph 0182-0184
[3]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - WO2021/58759, 2021, A1 Location in patent: Page/Page column 73

51
[ 14794-31-1 ]
[ 5700-60-7 ]
C₂₆H₃₂N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide In dichloromethane at 0℃;	1 Example 1: Synthesis of chelating agent I-2 in structural formula (I) The 1,2-diphenyl-ethylenediamine (2.12g, 10 mmol), NaOH (880mg, 22 mmol)was dissolved in 30 mL dichloromethane at 0Oadded acetyl chloride cinnamate (984 mg under C, 60 mmol) was stirred overnight.The reaction process was detected by TLC. After the reaction was completed, 2 M HCl was added to adjust pH 1, ethyl acetate was extracted (30 mL x 3), the organic phase was collected, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, spin-dried, 200-300 Mesh silica gel column chromatography to obtain 3.97g of target compound 1, yield 82%.

Reference： [1]Current Patent Assignee: FOURTH MILITARY MEDICAL UNIVERSITY - CN111138415, 2020, A Location in patent: Paragraph 0015

52
[ 5700-60-7 ]
C₂₂H₂₄N₂O₆ [ No CAS ]
C₃₆H₃₆N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	Stage #1: C₂₂H₂₄N₂O₆ With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Stage #2: 1,2-Diphenylethylenediamine With triethylamine In dichloromethane at 20℃; for 3h;	1 Take a dry 50 mL flask, weigh compound 2 (1.7 g, 4 mmol), add dichloromethane 20 mL, oxalyl chloride 2 mL, a drop of N, N dimethylformamide, a large amount of bubbles are generated, and the reaction is stirred at room temperature for 1 h Afterwards, spin dry for use.Take another dry 100 mL flask, add 20 mL of dichloromethane, 3 mL of triethylamine, 1,2 diphenylethane-1,2 diamine (2.12g, 10 mmol), and spin-dry the acid chloride with 10 mL Dichloromethane was dissolved, and it was slowly added to the reaction solution with a syringe, and a large amount of white smoke was generated.After reacting at room temperature for 3h, TLC detected that the raw material had reacted completely.Adjust pH 1 with 2M HCl, extract the reaction solution with dichloromethane (30 mL×3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, and rotovap under reduced pressure to obtain a light yellow oily liquid, 200~300 mesh Silica gel column chromatography (PE:EA=10:1~5:1) yielded 2.0 g of target compound 3 with a yield of 85%.

Reference： [1]Current Patent Assignee: FOURTH MILITARY MEDICAL UNIVERSITY - CN111138415, 2020, A Location in patent: Paragraph 0015; 0017

53
[ 5700-60-7 ]
[ 501-65-5 ]
3,3',4,4'-tetraphenyl-1,1'-biisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In methanol at 100℃; for 10h; Inert atmosphere;	2 Example 1: 3,3',4,4'-tetraphenyl-1,1'-biisoquinoline (3a) synthesis method 1: General procedure: Weighing benzil bisoxime(0.1 mmol, 24 mg),Diphenylacetylene (0.2 mmol, 36 mg),The feeding ratio is 1:2,[Cp*RhCl2]2 (1.6 mg, 2.5mol% equivalent to the amount of benzil bisoxime) as a catalyst,Sodium acetate (16 mg, 2 equivalents relative to the amount of benzil bisoxime) as the base,Add the protic solvent methanol (1 ml) as the reaction solvent,The reaction was performed at 100°C for 10 hours in a nitrogen atmosphere.After the reaction is complete, cool to room temperature, filter under reduced pressure,The white solid obtained after drying is the pure product 3,3',4,4'-tetraphenyl-1,1'-biisoquinoline (3a) with a yield of 93%.

Reference： [1]Current Patent Assignee: GUILIN UNIVERSITY OF TECHNOLOGY - CN111333572, 2020, A Location in patent: Paragraph 0017; 0018

54
[ 5700-60-7 ]
[ 92-44-4 ]
2,3-diphenyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium pyrosulfite; palladium 10% on activated carbon; water; ammonium formate at 100℃; Inert atmosphere; Schlenk technique;
65%	With sodium metabisulfite; sodium formate; palladium dichloride In water at 150℃; for 18h;	8 In the reaction vessel, mix 2,3-Dinaphthol (5mmol, 1.3g), 1,2-diphenylethylenediamine (2mmol, 0.42g), PdCl2 (0.1mol, 0.02g), sodium metabisulfite (2mmol , 0.38g), sodium formate (6mmol, 0.41g), and water (10mL) were mixed uniformly, reacted at 150°C for 18 hours, cooled to room temperature after the reaction was completed, filtered and evaporated under reduced pressure to remove unreacted materials to obtain a crude product. The crude product is purified by column chromatography to obtain 2,3-diphenyl-1,2,3,4-tetrahydrobenzo[g]quinoxaline(3h), which is compound 3h. Compound 3h is brown oil with a yield of 65%.

Reference： [1]Liang, Wanyi; Xie, Feng; Yang, Zhihai; Zeng, Zheng; Xia, Chuanjiang; Li, Yibiao; Zhu, Zhongzhi; Chen, Xiuwen [Organic Letters, 2020, vol. 22, # 21, p. 8291 - 8295]
[2]Current Patent Assignee: WUYI UNIVERSITY - CN111792999, 2020, A Location in patent: Paragraph 0125-0134

55
[ 5700-60-7 ]
[ 100-10-7 ]
C₃₂H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol for 5h;	2.3. Synthesis of Schiff base ligand (SN-NNDMB) A mixture of meso-1,2-diphenylethylenediamine (meso-stien)(5 mmol, 1.06 g) in MeOH (25 mL) was taken in a 100 mL RB flask.A solution of 4-N,N0-dimethylaminobenzaldehyde (10 mmol,1.49 g) in MeOH (25 mL) was then added slowly. The reaction mixturewas vigorously mixed for about 5 h. The formed precipitatewas collected by vacuum filtration and then washed several timesusing anhydrous ether and dried using a desiccator containinganhydrous CaCl2. The purity of the ligand was analyzed by TLC.The isolated yield of the ligand was found to be ~ 70% (1.66 g).Light yellow crystals, 1H NMR (CDCl3) d: 7.8 (s CH = N), 2.9 (s, N-(CH3)2), 6.6-7.5 (m, ArH), 4.6 (s, CH-N). IR (KBr, cm-1) m: 1605(CN), 1367 (CAN), 1444 (N-CH3), 3025 (Ar CH). Anal. calcd forC32H34N4: C 80.98, H 7.22, N 11.80; found: C 81.21, H 6.85, N12.12. UV-vis (CH2Cl2): k/nm 328, 402. Mass: m/z 475.

Reference： [1]Arish, D.; Bhuvanesh, N.; Kumaresan, S.; Shiju, C. [Polyhedron, 2021, vol. 205]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5700-60-7	MDL No. :	MFCD00709169
Formula :	C₁₄H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PONXTPCRRASWKW-UHFFFAOYSA-N
M.W :	212.29	Pubchem ID :	110695
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5700-60-7 ] {[proInfo.proName]}

Quality Control of [ 5700-60-7 ]

Related Doc. of [ 5700-60-7 ]

Product Details of [ 5700-60-7 ]

Safety of [ 5700-60-7 ]

Application In Synthesis of [ 5700-60-7 ]

[ 5700-60-7 ] Synthesis Path-Downstream 1~55

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry