ChemicalBook CAS DataBase List 2-BROMO-4-METHYLPHENYLTHIOUREA

2-BROMO-4-METHYLPHENYLTHIOUREA synthesis

6synthesis methods

Product Name:2-BROMO-4-METHYLPHENYLTHIOUREA
CAS Number:66644-79-9
Molecular formula:C8H9BrN2S
Molecular Weight:245.14

Benzenecarbothioic acid, anhydrosulfide with thiocyanic acid

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583-68-6 Synthesis

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Yield:-

Reaction Conditions:

Stage #1: benzoyl isothiocyanate;2-bromo-p-toluidine in acetone at 75; for 0.5 h;
Stage #2: with sodium hydroxide in water monomer at 80; for 0.5 h;

Steps:

4.2.2 General procedure to synthesize thioureas 11a-t

General procedure: Ammonium thiocyanate (2.43mmol) was dissolved in acetone (8mL) and the benzoyl chloride (2.29mmol) was added. After refluxing for 15min, the mixture was allowed to reach room temperature and the corresponding amine (1.62mmol) was added. The solution was refluxed for 30min, cooling down to room temperature, poured into cold water and stirred for another 30min. The mixture was filtered and the solid obtained was washed with water (3mL×3), then dried and dissolved in an aqueous solution of 10% NaOH (5mL). The solution was stirred at 80°C for half an hour and then cooled down to room temperature. Hydrochloric acid 6N was slowly added while pH was adjusted to 1-2 and the mixture was stirred for another 30min. After adjustment of the pH to 10 with ammonium hydroxide, the mixture was filtered and the precipitate obtained was washed with water (3mL×3) and then purified with petroleum ether: ethyl acetate (3:1 or 1:1) through a flash column chromatography to give the pure product.

References:

Xu, Zhichao;Tang, Qi;Xu, Ting;Cai, Yang;Lei, Ping;Chen, Yinuo;Zou, Wenting;Dong, Chune;Lan, Ke;Wu, Shuwen;Zhou, Hai-Bing [Bioorganic Chemistry,2022,vol. 122,art. no. 105683]