191849-71-5|3-Ethoxybenzene-1,2-diamine| Ambeed

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Quality Control of [ 191849-71-5 ] Purity: 95% SDS Specification

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Product Details of [ 191849-71-5 ]

CAS No. :	191849-71-5
Formula :	C₈H₁₂N₂O
M.W :	152.19
SMILES Code :	NC1=CC=CC(OCC)=C1N
MDL No. :	MFCD09701449
InChI Key :	GBMGXXPFNLJLMP-UHFFFAOYSA-N
Pubchem ID :	437573

Safety of [ 191849-71-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 191849-71-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 191849-71-5 ]

[ 191849-71-5 ] Synthesis Path-Downstream 1~23

1
[ 4280-24-4 ]
[ 191849-71-5 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20.0℃; for 15.0h;Inert atmosphere;	2,3-dinitrophenylethyl ether (1 g, 4.71 mmol)Dissolved in 20 ml of ethyl acetate / methanol = 8:1 mixed solvent,10% Pd-C (180 mg) was added under a nitrogen atmosphere, and the reaction system was replaced with hydrogen three times.Stir at room temperature for 15 hours. Filtration to remove palladium carbon,The filtrate is concentrated to give 3-ethoxy-1,2-phenylenediamine(694 mg, yield 96.7%).

References: [1]Patent: CN103435561,2016,B .Location in patent: Paragraph 0278; 0280.
[2]Journal of the Chemical Society,1953,p. 2816,2819.

2
[ 4280-24-4 ]
[ 191849-71-5 ]
3-ethoxy-2-nitro-aniline [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1946,vol. 65,p. 361,378.
Recueil des Travaux Chimiques des Pays-Bas,1943,vol. 62,p. 203.

3
[ 191849-71-5 ]
[ 517-21-5 ]
[ 18514-74-4 ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 4450.
[2]Journal of the Chemical Society,1953,p. 2816,2819.

4
[ 191849-71-5 ]
[ 431-03-8 ]
5-ethoxy-2,3-dimethyl-quinoxaline [ No CAS ]

References: [1]Journal of the Chemical Society,1953,p. 2822,2827.

5
[ 191849-71-5 ]
4-Chloro-N-ethoxy-benzamide; hydrochloride [ No CAS ]
2-(4-chlorophenyl)-4⁽⁷⁾-ethoxy-1H-benzimidazole [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 635 - 642.

7
[ 191849-71-5 ]
2-(4-chlorophenyl)-4⁽⁷⁾-hydroxy-1H-benzimidazole [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 635 - 642.

8
[ 191849-71-5 ]
5-ethoxy-quinoxaline-1-oxide [ No CAS ]

References: [1]Journal of the Chemical Society,1953,p. 2816,2819.

9
[ 381-73-7 ]
[ 191849-71-5 ]
[ 1188914-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		solution of 1.64 g (9 mmol) of 2-ethoxy-6-nitroaniline in methanol was hydrogenated over palladium on carbon. After filtration through celite, the solution was acidified with cone. HCl and evaporated to dryness. The residue was combined with 1.73 g (18 mmol) of difluoroacetic acid in 10 mL 4 M HCl and the solution was heated under reflux for 4 hrs. After dilution with water, decolorization with charcoal, and filtration through celite, the cooled solution was made basic with cone, aqueous ammonia to give 1.29 g (68 % yield) of 2-(difluoromethyl)-4-ethoxy-lH-benzimidazole: mp (MeOη/η2O) 185-187 0C; 1H NMR (DMSO-^5) (tautomeric mixture) δ 13.30 (m, exchangeable with D2O, IH), 7.20 (t, 7HF = 53.3 Hz, IH), 7.19 (m, 2 H), 6.78 (br d, J = 7.5 Hz, IH), 4.24 (q, J = 7.0 Hz, 2H), 1.41 (t, J = 7.0 Hz, 3H); MS (APCI+) 213.3 (MH+); Anal. Calcd. for C0H10F2N2O: C, 56.6; H, 4.75; N, 13.2; Found: C, 56.9; H, 4.8; N, 13.4%.

References: [1]Patent: WO2009/120094,2009,A2 .Location in patent: Page/Page column 48; 86.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 7105 - 7126.

10
[ 6036-46-0 ]
[ 191849-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium on activated charcoal; In methanol;	solution of 1.64 g (9 mmol) of 2-ethoxy-6-nitroaniline in methanol was hydrogenated over palladium on carbon. After filtration through celite, the solution was acidified with cone. HCl and evaporated to dryness. The residue was combined with 1.73 g (18 mmol) of difluoroacetic acid in 10 mL 4 M HCl and the solution was heated under reflux for 4 hrs. After dilution with water, decolorization with charcoal, and filtration through celite, the cooled solution was made basic with cone, aqueous ammonia to give 1.29 g (68 % yield) of 2-(difluoromethyl)-4-ethoxy-lH-benzimidazole: mp (MeOη/η2O) 185-187 0C; 1H NMR (DMSO-^5) (tautomeric mixture) δ 13.30 (m, exchangeable with D2O, IH), 7.20 (t, 7HF = 53.3 Hz, IH), 7.19 (m, 2 H), 6.78 (br d, J = 7.5 Hz, IH), 4.24 (q, J = 7.0 Hz, 2H), 1.41 (t, J = 7.0 Hz, 3H); MS (APCI+) 213.3 (MH+); Anal. Calcd. for C0H10F2N2O: C, 56.6; H, 4.75; N, 13.2; Found: C, 56.9; H, 4.8; N, 13.4%.
3.26 g	With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃;	To a stirred solution of 92b (3.560 g, 19.54 mmol) in MeOH was added 10% Pd-C(0.775 g). After stirring at room temperature overnight under a hydrogen atmosphere, thereaction mixture was filtered through a pad of Celite. The filtrate was concentrated invacuo to give the intermediate diamine (3.260 g, 24.42 mmol), which was then dissolvedin TFA (75 mL) initially at 0 C. The resulting mixture was subsequently stirred overnightunder reflux conditions before concentration to a residue in vacuo. The residue wasdissolved in EtOAc and the resulting solution was poured into saturated NaHCO3 aq. Theorganic layer was separated, dried over Na2SO4, and concentrated in vacuo to give 93b(2.300 g, 52% yield).

References: [1]Patent: WO2009/120094,2009,A2 .Location in patent: Page/Page column 48; 86.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 7105 - 7126.
[3]Molecules,2022,vol. 27.

11
[ 191849-71-5 ]
2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-4-ethoxy-1H-benzimidazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7105 - 7126.

12
[ 191849-71-5 ]
[ 1188914-97-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7105 - 7126.

13
[ 849585-22-4 ]
[ 191849-71-5 ]
1-(7-ethoxy-1H-benzimidazol-2-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride; In water; for 3.0h;Reflux;	A 50 mL round bottom flask was charged 7.6 g (0.05 mol) of <strong>[191849-71-5]3-ethoxybenzene-1,2-diamine</strong>,4.5 g (0.05 mol) of lactic acid and 20 ml of 4 mol / L hydrochloric acid,Heating reflux 3h,Cool to room temperature.With concentrated ammonia and purple purple litmus paper turned red,Filter out the solid,Recrystallization from water (73%).To a 50 mL three-necked flask was added 4.12 g (0.02 mol) of 1- (7-ethoxy-1H-benzimidazol-2-ethyl) alcohol and 15 mL of glacial acetic acid,After heating to 90 C, an aqueous solution of CrO3 was added dropwise to the three-necked flask,After dripping,The temperature was stirred at 105 for 20 min,The reaction was then poured into a beaker containing 200 mL of water,Stirring for a moment,Filter,The filtrate was extracted three times with chloroform,The chloroform layers were combined,Dried over anhydrous magnesium sulfate,The filtrate was evaporated to dryness to give a yellow solid,Recrystallization from toluene,Yield: 71%20 ml of 95% ethanol and 4.08 g (0.02 mol) of 1- (7-methoxy-1H-benzimidazol-2-ethyl) ketone were added to a 50 ml round-Stir for about 10 min to completely dissolve the solid,Further, 8 ml of a 10% aqueous solution of sodium hydroxide was added,0.02 mol of benzaldehyde was added with stirring,After a period of time the system precipitates a lot of solid,The reaction end point was detected by TLC,After the reaction, the solid was filtered to obtain a solid, yield: 84%.

References: [1]Patent: CN104140415,2017,B .Location in patent: Paragraph 0323.

14
[ 191849-71-5 ]
1-(7-ethoxy-1H-benzimidazol-2-yl)ethanone [ No CAS ]

References: [1]Patent: CN104140415,2017,B .

15
[ 191849-71-5 ]
C₁₈H₁₆N₂O₂ [ No CAS ]

References: [1]Patent: CN104140415,2017,B .

16
[ 66-56-8 ]
[ 191849-71-5 ]

References: [1]Patent: CN103435561,2016,B .

17
[ 553-90-2 ]
[ 191849-71-5 ]
5-ethoxyquinoxaline-2,3(1H,4H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.1%	Reflux;	3-Ethoxy-1,2-phenylenediamine (300 mg, 1.66 mmol)Mixed with 20 ml of dimethyl oxalate,Warm to reflux and stir for 3-4 hours.After the reaction solution was cooled, the resulting solid was filtered off.The solid was dispersed in 15 ml of N,N-dimethylformamide.Add 1 g of activated carbon, warm to reflux, and filter while hot for 1 hour.Add 1 ml of water to the filtrate.Allow to stand for 1 hour,The precipitated white solid is filtered,Washed with water, washed with 95% ethanol,Washing with ethyl acetate to give 5-ethoxyquinoxaline-2,3-dione white solid(240 mg, yield 59.1%).

References: [1]Patent: CN103435561,2016,B .Location in patent: Paragraph 0278; 0281; 0282.

18
[ 191849-71-5 ]
4-(4-chloro-6-(4-ethoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine [ No CAS ]