4-AMINO-N-(4-METHYLPHENYL)BENZAMIDE synthesis

7synthesis methods

Product Name:4-AMINO-N-(4-METHYLPHENYL)BENZAMIDE
CAS Number:955-96-4
Molecular formula:C14H14N2O
Molecular Weight:226.27

106-49-0
390 suppliers
$5.00/5G

16106-38-0
27 suppliers
$120.00/100mg

955-96-4
19 suppliers
$45.00/50mg

Yield:955-96-4 86%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 25;

Steps:

4.1.1 General procedure A for the synthesis of compound I-1～I-9

General procedure: A mixture of 4-aminobenzoic acid 1 (6.86g, 50.02mmol) and sulfurous dichloride (36.31mL, 50.02mmol) was heated to 70°C for 1.5h, solvent was removed under reduced pressure gave 2 as yellow oil (7.12g, 91.5% yield). To a solution of the intermediate 2 (5.00g, 32.14mmol) in anhydrous dichloromethane (20mL) was added a suspension of 3a-3i (32.14mmol) in anhydrous dichloromethane (20mL) and triethylamine (5.34mL, 38.57mmol) at 0°C, the reaction mixture was stirred at ambient temperature overnight. After completion of the reaction, the mixture was extracted with dichloromethane twice, the combined organic phases were washed with water and aqueous sodium chloride respectively, dried over anhydrous Na₂SO₄ and purified by silica gel column chromatography (PE: EA=5:1) to give 4a-4i

References:

Huang, Lei;Li, Xiaofei;Wu, Huanhuan;Wu, Xingxin;Xu, Qiang;Xu, Shuaiqi;Xu, Yizhu;Zhai, Bingxin;Zhu, Qihua [European Journal of Medicinal Chemistry,2022,vol. 237,art. no. 114417]