Reaction #619088

Reaction equation

N-bromosuccinimide

dicyclohexylamine

(2-amino-4-thiazolyl)acetic acid ethyl ester

acetic acid

→

title compound

[5-Bromo-2-(3,3-dicyclohexyl-ureido)-thiazol-4-yl]-acetic acid ethyl ester

[2-(3,3-Dicyclohexyl-ureido)-thiazol-4-yl]-acetic acid ethyl ester

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONredissolved in dichloromethane
3. 3
   Washwashed with 10% sodium sulphate, water, aqueous sodium bicarbonate, brine
4. 4
   Dryingdried over magnesium sulphate

Procedure

[2-(3,3-Dicyclohexyl-ureido)-thiazol-4-yl]-acetic acid ethyl ester was prepared from dicyclohexylamine and (2-amino-4-thiazolyl)acetic acid ethyl ester as described in general procedure (A). To this compound was added 1.3 equivalents of N-bromosuccinimide suspended in acetic acid, and the mixture was stirred for 3 h at RT. The reaction mixture was concentrated in vacuo, redissolved in dichloromethane, washed with 10% sodium sulphate, water, aqueous sodium bicarbonate, brine and then dried over magnesium sulphate. Flash chromatography afforded the title compound.

Source