Name: 15516-47-9|(4-Methylphenoxy)acetyl chloride|97%
Brand: Ambeed
SKU: A711547
Rating: 97 (30 reviews)

1
[ 940-64-7 ]
[ 15516-47-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride In benzene at 50℃; for 3h;
94%	With thionyl chloride In benzene for 3h; Reflux;	5 p-Tolyloxy-acetyl chloride (SO1 -140) (5a): To a solution of p-tolyoxy-acetic acid (4a) (300 mg, 1 .81 mmol) in 20 ml benzene thionyl chloride (5 mL) was added and the mixture was refluxed for 3h till a clear solution was formed. Excess thionyl chloride and benzene were evaporated to give the pure compound SO1 -140 5a as colorless liquid (313 mg, 94%). 1 H NMR (400 M Hz, CDCI3) δ 7.1 1 (dd, J = 8.7, 0.6 Hz, 1 H), 6.80 (d, J = 8.7 Hz, 1 H), 4.92 (d, J = 3.4 Hz, 1 H), 2.30 (s, 3H).
94%	With thionyl chloride In benzene for 3h; Reflux;

93%	With oxalyl dichloride In dichloromethane at 0 - 20℃;	21a To a 0°C stirring suspension of 4.00 g of the acid (24.07 mmol; 1.0 eqmol) in 40.0 mL of dichloromethane, it was added 2.20 mL of oxalyl chloride (25.27 mmol; 1.05 eqmol) and then 56 uL of dimethylformamide (0.7221 mmol; 0.03 eqmol). The ice bath was removed and the reaction was allowed to stir at room temperature until gas evolution ceased (bubbler monitor).All the volatiles were then evaporated in vacuo. The obtained crude liquid contained some very fine precipitate, so the neat liquid was passed over a Celite pad which was flushed with hexanes. Once again, all the volatiles were then evaporated in vacuo, to obtain a clear liquid which showed only one compound at the 1H-NMR analysis. The obtained 4.129 g (22.36 mmol; 93%) were used in the next step without further purification. 1H NMR (400 MHz; CDCls) δ 2.30 (s, 3H), 4.92 (s, 2H), 6.84 - 6.76 (m, 2H), 7.15 - 7.08 (m, 2H).
93.2%	With thionyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 5h;	13 Preparation of 4-methylphenoxyacetyl chloride (5a) 2 ml of 4-methylphenoxyacetic acid (4a), 2 ml of sulfuryl sulfoxide, 50 ml of tetrahydrofuran and 0.1 ml of DMF were placed in a reaction flask and reacted at 50C for 5 hours. The reaction was completed and the reaction was dry to obtain 2.07 g of a pale yellow liquid , The yield was 93.2%.
93.2%	With thionyl chloride In tetrahydrofuran at 50℃; for 5h;	15 4Preparation of methylphenoxyacetyl chloride (9a) 2 g of 4-methylphenoxyacetic acid (8a), 2 ml of thionyl chloride, 50 ml of tetrahydrofuran and 0.1 ml of DMF were placed in a reaction flask and reacted at 50 ° C for 5 hours. The reaction was completed and the reaction was dry to obtain a pale yellow liquid 2.07 g, yield 93.2%. m / z (ESI) = 185.5 [M + H] & lt; + & gt ;.
	With thionyl chloride
	With thionyl chloride In ethyl acetate; benzene for 8h; Heating;
	With thionyl chloride for 4h; Heating;
	With thionyl chloride In methanol; ethyl acetate for 7h; Heating;
	With thionyl chloride In methanol; ethyl acetate; benzene for 8h; Heating;
	With thionyl chloride for 8h; Heating;
	With thionyl chloride In chloroform Heating;
	With thionyl chloride In benzene Heating;
	With thionyl chloride; N,N-dimethyl-formamide In chlorobenzene Heating;
	With thionyl chloride for 5h; Heating;
	With dmap; thionyl chloride In dichloromethane for 2h; Reflux;
	With thionyl chloride
	With thionyl chloride for 6h; Reflux;
	With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h;	General procedure for the synthesis of HY-1a-HY-1f General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f
	With thionyl chloride for 5h; Reflux;	General procedure for preparation of 5-R-4-R₁-2-nitrobenzoylchlorides 12a-c and 2-phenoxyacetyl chlorides 16a-e General procedure: Substituted benzoyl and phenoxyacetyl chlorides 12a-c and 16a-e were obtained by refluxing for 5 h the appropriate acid derivatives (0.01 mol) with thionyl chloride (7.25 mL). After evaporation under reduced pressure, the crude liquid residue was used for subsequent reactions without purification.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	General synthetic procedure for compounds 8-11 and 13-36 General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 °C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 °C. The solution was stirred for another 2 hrs at 25 °C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.
	With thionyl chloride at 65 - 70℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;
	With thionyl chloride Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h;

Reference： [1]Ito, Kazuaki; Takasawa, Toshiro; Ohba, Yoshihiro [Synthetic Communications, 2002, vol. 32, # 24, p. 3839 - 3849]
[2]Current Patent Assignee: H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE - WO2012/129564, 2012, A2 Location in patent: Page/Page column 61-62
[3]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[4]Current Patent Assignee: Firmenich International SA - WO2012/61698, 2012, A2 Location in patent: Page/Page column 62
[5]Current Patent Assignee: NANJING HUAMAI BIO PHARMACEUTICAL TECH - CN106146450, 2016, A Location in patent: Paragraph 0087; 0088; 0089
[6]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN104672192, 2017, B Location in patent: Paragraph 0093; 0094; 0095
[7]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541]
[8]Jain; Srivastava [Journal of the Indian Chemical Society, 1990, vol. 67, # 9, p. 775 - 776]
[9]Hajela Km.; Sengupta; Shanker; Doval [Archiv der Pharmazie, 1983, vol. 316, # 5, p. 431 - 434]
[10]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[11]Chaurasia; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 2, p. 106 - 107]
[12]Chaurasia, Sunita; Srivastava, Savitri D. [Journal of the Indian Chemical Society, 1992, vol. 69, # 1, p. 45 - 46]
[13]Bhatt, P.; Srivastava, S. D.; Mehta, P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 514 - 516]
[14]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]
[15]Vorob'ev; Kurbatov; Krasnikov; Mezheritskii; Usova [Russian Chemical Bulletin, 2006, vol. 55, # 8, p. 1492 - 1497]
[16]Han, Liang; Gao, Jian-Rong; Li, Zheng-Ming; Zhang, Yun; Guo, Wei-Ming [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3231 - 3234]
[17]Location in patent: experimental part Jimenez, Fabiola; Cruz, Maria Del Carmen; Zuniga, Clara; Martinez, Maria A.; Chamorro, German; Diaz, Francisco; Tamariz, Joaquin [Medicinal Chemistry Research, 2010, vol. 19, # 1, p. 33 - 57]
[18]Location in patent: scheme or table He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[19]Location in patent: experimental part Han, Liang; Zhu, Qiong-Yan; Jia, Jian-Hong; Li, Yu-Jin; Gao, Jian-Rong [Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1223 - 1226]
[20]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]
[21]Raffa, Demetrio; Maggio, Benedetta; Plescia, Fabiana; Cascioferro, Stella; Raimondi, Maria Valeria; Cancemi, Gabriella; D'Anneo, Antonella; Lauricella, Marianna; Cusimano, Maria Grazia; Bai, Ruoli; Hamel, Ernest; Daidone, Giuseppe [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6305 - 6316]
[22]Li, Zheng; Wang, Xuekun; Xu, Xue; Yang, Jianyong; Qiu, Qianqian; Qiang, Hao; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6666 - 6672]
[23]Mo, Wenyan; Shi, Yanxia; He, Junbo; Li, Baoju; Peng, Hao; He, Hongwu [Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187]
[24]Kuznetsov, Dmitry M.; Mukhina, Olga A.; Kutateladze, Andrei G. [Angewandte Chemie - International Edition, 2016, vol. 55, # 24, p. 6988 - 6991][Angew. Chem., 2016, vol. 128, # 24, p. 7102 - 7105,4]
[25]Sheng, Xijun; Zhou, Yuan; Zhang, Shasha; Peng, Hao; He, Hongwu [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 165 - 170]
[26]Noncovich, Alain; Priest, Chad; Ung, Jane; Patron, Andrew P.; Servant, Guy; Brust, Paul; Servant, Nicole; Faber, Nathan; Liu, Hanghui; Gonsalves, Nicole S.; Ditschun, Tanya L. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3931 - 3938]
[27]Lei, Kang; Li, Pan; Yang, Xue-Fang; Wang, Shi-Ben; Wang, Xue-Kun; Hua, Xue-Wen; Sun, Bin; Ji, Lu-Sha; Xu, Xiao-Hua [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 37, p. 10489 - 10497]

2
[ 30709-67-2 ]
[ 15516-47-9 ]
[ 72192-53-1 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524

3
[ 15516-47-9 ]
[ 16942-66-8 ]
[ 72192-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Osman; Hassan Kh.; El-Kashef; et al. [Journal of the Indian Chemical Society, 1979, vol. 56, # 5, p. 521 - 524]

4
[ 151-56-4 ]
[ 15516-47-9 ]
[ 78961-68-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine at 5℃;

Reference： [1]Shukla; Ahmad [Pharmazie, 1981, vol. 36, # 5, p. 327 - 328]

5
[ 908094-01-9 ]
[ 15516-47-9 ]
1-Diazo-3-p-tolyloxy-propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In diethyl ether for 4h; Ambient temperature;

Reference： [1]Saba, Antonio [Synthesis, 1984, # 3, p. 268 - 270]

6
[ 51-17-2 ]
[ 15516-47-9 ]
[ 92756-18-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With polyethylene glycol-400; potassium carbonate In acetonitrile for 2h; Ambient temperature;
64%	With sodium hydroxide In methanol

Reference： [1]Wang, Lailai; Lu, Shijie; Li, Shuben; Zhang, Youming; Wei, Taibao [Synthetic Communications, 1998, vol. 28, # 6, p. 1005 - 1011]
[2]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]

7
[ 92-84-2 ]
[ 15516-47-9 ]
[ 41648-61-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide In methanol; diethyl ether; ethyl acetate

Reference： [1]Chaurasia; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 2, p. 106 - 107]

8
[ 18730-32-0 ]
[ 15516-47-9 ]
[ 86149-04-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydroxide In ethanol 2.) reflux, 6 h;

Reference： [1]Hajela Km.; Sengupta; Shanker; Doval [Archiv der Pharmazie, 1983, vol. 316, # 5, p. 431 - 434]

9
[ 364-62-5 ]
[ 15516-47-9 ]
[ 65569-53-1 ]

Yield	Reaction Conditions	Operation in experiment
50.3%	With triethylamine In toluene for 6h; Heating;

Reference： [1]Metz; Pindell; Chen [Journal of Medicinal Chemistry, 1983, vol. 26, # 7, p. 1065 - 1070]

10
[ 15516-47-9 ]
[ 75129-91-8 ]
[ 86148-97-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydroxide In ethanol 2.) reflux, 6 h;

Reference： [1]Hajela Km.; Sengupta; Shanker; Doval [Archiv der Pharmazie, 1983, vol. 316, # 5, p. 431 - 434]

11
[ 15516-47-9 ]
[ 84496-23-1 ]
[ 84496-28-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In 1,4-dioxane for 2h; Heating;

Reference： [1]Osman, A. M.; Youssef, M. S. K.; Atta, F. M. [Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 953 - 956]

12
[ 15516-47-9 ]
[ 86148-88-1 ]
[ 86148-96-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide In ethanol 2.) reflux, 6 h;

Reference： [1]Hajela Km.; Sengupta; Shanker; Doval [Archiv der Pharmazie, 1983, vol. 316, # 5, p. 431 - 434]

13
[ 15516-47-9 ]
[ 18741-24-7 ]
[ 86148-92-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide In ethanol 2.) reflux, 6 h;

Reference： [1]Hajela Km.; Sengupta; Shanker; Doval [Archiv der Pharmazie, 1983, vol. 316, # 5, p. 431 - 434]

14
[ 15516-47-9 ]
[ 16640-68-9 ]
[ 114914-29-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine hydrochloride In toluene Ambient temperature;

Reference： [1]Rehman, H.; Rao, Jampani Madhusudana [Synthetic Communications, 1987, vol. 17, # 9, p. 1119 - 1128]

15
[ 15516-47-9 ]
[ 2735-62-8 ]
2-(1-Methyl-1H-benzoimidazol-2-yl)-3-oxo-4-p-tolyloxy-butyronitrile [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 445 - 447

16
[ 15516-47-9 ]
[ 16883-23-1 ]
2-p-Tolyloxy-1-[2-(2,4,5-trichloro-phenoxymethyl)-benzoimidazol-1-yl]-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With polyethylene glycol-400; potassium carbonate In acetonitrile for 2h; Ambient temperature;

Reference： [1]Wang, Lailai; Lu, Shijie; Li, Shuben; Zhang, Youming; Wei, Taibao [Synthetic Communications, 1998, vol. 28, # 6, p. 1005 - 1011]

17
[ 15516-47-9 ]
[ 3156-21-6 ]
1-[2-(2,4-Dichloro-phenoxymethyl)-benzoimidazol-1-yl]-2-p-tolyloxy-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With polyethylene glycol-400; potassium carbonate In acetonitrile for 2h; Ambient temperature;

Reference： [1]Wang, Lailai; Lu, Shijie; Li, Shuben; Zhang, Youming; Wei, Taibao [Synthetic Communications, 1998, vol. 28, # 6, p. 1005 - 1011]

18
[ 616-45-5 ]
[ 15516-47-9 ]
1-(2-p-Tolyloxy-acetyl)-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydroxide In methanol; acetone; toluene

Reference： [1]Bhatt, P.; Srivastava, S. D.; Mehta, P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 514 - 516]

19
[ 15516-47-9 ]
[ 1147550-11-5 ]
4-tolyloxyacetyl isothiocyanate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyethylene glycol-400 In dichloromethane at 20℃; for 1h;

Reference： [1]Wang; Li; Da [Synthetic Communications, 2001, vol. 31, # 1, p. 19 - 26]

20
[ 15516-47-9 ]
[ 107-15-3 ]
2-p-tolyloxy-N-[2-(2-p-tolyloxy-acetylamino)-ethyl]-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.6%	With triethylamine In benzene at 20℃; for 2h;

Reference： [1]Deng, Sheng Lou; Chen, Ru Yu; Liu, Dong Zhi [Journal of Chemical Crystallography, 2001, vol. 31, # 9-10, p. 453 - 458]

21
[ 15516-47-9 ]
[ 2577-90-4 ]
3-phenyl-2-(2-p-tolyloxy-acetylamino)-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With pyridine In chloroform at 20℃; for 24h;

Reference： [1]Ito, Kazuaki; Takasawa, Toshiro; Ohba, Yoshihiro [Synthetic Communications, 2002, vol. 32, # 24, p. 3839 - 3849]

22
[ 15516-47-9 ]
[ 229978-36-3 ]
N-(5-methyl-isoxazol-3-yl)-2-(2-p-tolyloxy-acetylamino)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine In acetonitrile for 2h; Heating;

Reference： [1]Raffa; Migliara; Daidone; Maggio; Schiilaci [Bollettino Chimico Farmaceutico, 2002, vol. 141, # 1, p. 3 - 7]

23
[ 15516-47-9 ]
[ 496843-88-0 ]
N-(5-methyl-isoxazol-3-yl)-3-(2-p-tolyloxy-acetylamino)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine In acetonitrile for 2h; Heating;

Reference： [1]Raffa; Migliara; Daidone; Maggio; Schiilaci [Bollettino Chimico Farmaceutico, 2002, vol. 141, # 1, p. 3 - 7]

24
[ 15516-47-9 ]
[ 496843-89-1 ]
N-(5-methyl-isoxazol-3-yl)-4-(2-p-tolyloxy-acetylamino)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In acetonitrile for 2h; Heating;

Reference： [1]Raffa; Migliara; Daidone; Maggio; Schiilaci [Bollettino Chimico Farmaceutico, 2002, vol. 141, # 1, p. 3 - 7]

25
[ 15516-47-9 ]
[ 17674-28-1 ]
dimethyl α-(4-methylphenoxyacetoxy)vinyl phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Liu, Hui; Zhou, Yong-Gui; Yu, Zheng-Kun; Xiao, Wen-Jing; Liu, Sheng-Hua; He, Hong-Wu [Tetrahedron, 2006, vol. 62, # 48, p. 11207 - 11217]

26
[ 15516-47-9 ]
[ 142-78-9 ]
C₂₃H₃₇NO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3231 - 3234

27
[ 111-57-9 ]
[ 15516-47-9 ]
C₂₉H₄₉NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine In chloroform at 20℃; for 12h;

Reference： [1]Han, Liang; Gao, Jian-Rong; Li, Zheng-Ming; Zhang, Yun; Guo, Wei-Ming [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3231 - 3234]

28
[ 79-20-9 ]
[ 15516-47-9 ]
methyl 4-(4-methylphenoxy)acetoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: acetic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: 2-(4-methylphenoxy)acetyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 14h; Further stages.;

Reference： [1]Rashid, Muhammad A.; Rasool, Nasir; Adeel, Muhammad; Reinke, Helmut; Spannenberg, Anke; Fischer, Christine; Langer, Peter [Tetrahedron, 2008, vol. 64, # 3, p. 529 - 535]

29
[ 67028-40-4 ]
[ 15516-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / tetramethylammonium hydroxide / tetrahydrofuran; H₂O / 24 h / Heating 2: 98 percent / thionyl chloride / benzene / 3 h / 50 °C
	Multi-step reaction with 2 steps 1: sodium hydroxide; ethanol / Reflux 2: thionyl chloride / benzene / 3 h / Reflux
	Multi-step reaction with 2 steps 1.1: sodium hydroxide / 2 h / Reflux 1.2: pH 1 2.1: thionyl chloride / benzene / 3 h / Reflux

Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol; water / 1.5 h / 20 °C 2: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 5 h / 50 °C

Reference： [1]Ito, Kazuaki; Takasawa, Toshiro; Ohba, Yoshihiro [Synthetic Communications, 2002, vol. 32, # 24, p. 3839 - 3849]
[2]Current Patent Assignee: H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE - WO2012/129564, 2012, A2
[3]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[4]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]

30
[ 106-44-5 ]
[ 15516-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOH / H₂O / 2 h 2: SOCl₂ / benzene / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

31
[ 15516-47-9 ]
3-amino-2-p-tolyloxymethyl-3H-quinazolin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating 3: ethanol / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

32
[ 15516-47-9 ]
[ 1026026-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

33
[ 15516-47-9 ]
3-amino-5,6-dimethyl-2-p-tolyloxymethyl-3H-thieno[2,3-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating 3: ethanol / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

34
[ 15516-47-9 ]
N-(3-hydrazinocarbonyl-4,5-dimethyl-thiophen-2-yl)-2-p-tolyloxy-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

35
[ 15516-47-9 ]
3-amino-2-p-tolyloxymethyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating 3: ethanol / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

36
[ 15516-47-9 ]
[ 1027219-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid / 1 h / 0 - 5 °C 2: N₂H₄*H₂O / ethanol / 6 h / Heating

Reference： [1]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]

37
[ 106-44-5 ]
[ 15516-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alkali 2: thionyl chloride
	Multi-step reaction with 2 steps 1: sodium hydroxide 2: thionyl chloride
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 1 h / Reflux 2: thionyl chloride / 6 h / Reflux

	Multi-step reaction with 3 steps 1: potassium carbonate / acetone / Reflux 2: sodium hydroxide; ethanol / Reflux 3: thionyl chloride / benzene / 3 h / Reflux
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 14 h / Reflux 2.1: sodium hydroxide / 2 h / Reflux 2.2: pH 1 3.1: thionyl chloride / benzene / 3 h / Reflux
	Multi-step reaction with 3 steps 1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 12 h / 75 °C 2: potassium hydroxide / ethanol; water / 1.5 h / 20 °C 3: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 5 h / 50 °C
	Multi-step reaction with 2 steps 1: sodium hydroxide / water / 100 - 110 °C 2: thionyl chloride / 65 - 70 °C
	Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / acetone; N,N-dimethyl-formamide / 12 h / Reflux 2: potassium hydroxide; ethanol / 12 h / 20 °C 3: thionyl chloride / N,N-dimethyl-formamide; tetrahydrofuran / 5 h / 50 °C
	Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / acetone / 12 h / Reflux 2: potassium hydroxide / ethanol / 12 h / 20 °C 3: thionyl chloride / tetrahydrofuran / 5 h / 50 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C 1.2: 12 h / 50 °C 2.1: lithium hydroxide / methanol; water / 12 h / 50 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h / 20 °C

Reference： [1]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541]
[2]He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[3]Han, Liang; Zhu, Qiong-Yan; Jia, Jian-Hong; Li, Yu-Jin; Gao, Jian-Rong [Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1223 - 1226]
[4]Current Patent Assignee: H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE - WO2012/129564, 2012, A2
[5]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[6]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]
[7]Mo, Wenyan; Shi, Yanxia; He, Junbo; Li, Baoju; Peng, Hao; He, Hongwu [Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187]
[8]Current Patent Assignee: NANJING HUAMAI BIO PHARMACEUTICAL TECH - CN106146450, 2016, A
[9]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN104672192, 2017, B
[10]Lei, Kang; Li, Pan; Yang, Xue-Fang; Wang, Shi-Ben; Wang, Xue-Kun; Hua, Xue-Wen; Sun, Bin; Ji, Lu-Sha; Xu, Xiao-Hua [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 37, p. 10489 - 10497]

38
aqueous sodium chloride [ No CAS ]
[ 15516-47-9 ]
[ 90719-32-7 ]
[ 144-55-8 ]
[ 406701-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane	R.20 (S)-4-Benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-one A 1.61N solution of n-butyl lithium in hexane (25.2 ml) was added dropwise at -78ØC to a solution of (S)-4-benzyl-2-oxazolidinone (7.08 g) in tetrahydrofuran (70 ml), and after the completion of the dropwise addition, the reaction mixture was stirred at -78ØC for 30 minutes. To this resulting solution was added at -78ØC a solution of 4-methylphenoxyacetyl chloride obtained above in tetrahydrofuran (70 ml) followed by stirring at 0ØC for 1 hour. The resulting reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate layer was washed successively with a 1N aqueous solution of hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate = 3/1 ~ 1/1) to afford the target compound (9.00 g) as a colorless oil. 1H-NMR (270 MHz, CDCl3) δ (ppm) 2.30(3H, s), 2.84 (1H, dd, J=9.5, 13.5Hz), 3.36 (1H, dd, J=3.0, 13.5Hz), 4.25-4.37 (2H, m), 4.68-4.76 (1H, m), 5.22 (2H, s), 6.88 (2H, d, J=8.5Hz), 7.11 (2H, d, J=8.5Hz), 7.20-7.38 (5H, m).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1354602, 2003, A1

39
[ 79-37-8 ]
[ 940-64-7 ]
[ 15516-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; N,N-dimethyl-formamide	R.20 (S)-4-Benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-one (S)-4-Benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-one Oxalyl chloride (8.83 ml) and N,N-dimethylformamide (3 drops) were added at room temperature to a solution of 4-methylphenoxyacetic acid (6.73 g) in dichloromethane (70 ml), and the reaction mixture was stirred for 1.5 hours. The reaction solution was concentrated under reduced pressure, then the resulting acidic gas was removed as the toluene azeotrope, and the product was dried under reduced pressure to give 4-methylphenoxyacetyl chloride.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1354602, 2003, A1

40
C₂₆H₂₄NOP [ No CAS ]
[ 15516-47-9 ]
[ 1021153-53-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In 1,2-dichloro-ethane at -5 - 20℃; for 1.5h;