Bromo(phenyl)acetic acid → 2-Amino-5-phenyl-1,3-thiazol-4-one

HRID 346234Notes

Reaction equation

HRID 346234 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](O)=[O:4].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[NH:12]=[C:13]1[NH:15][C:3](=[O:4])[CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[S:14]1

Participants

4

Reactant 2

HCID 97919Bromo(phenyl)acetic acidHCID 2723790Thiourea

Product 1

HCID 1356332132-Amino-5-phenyl-1,3-thiazol-4-oneYield 157.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 100 g (0.47 mole) of α-bromophenylacetic acid (Aldrich) and 41.0 g (0.54 mole) of thiourea (Baker) in 600 mL of ethanol was stirred and heated on a steam bath for 4 hr. The solvent was evaporated under reduced pressure to give 142.0 g crude title compound as a white solid. An analytical sample of title compound, mp 249°-252° C., was prepared from 95% ethanol as white flakes.

Workup

  1. temperatureheated on a steam bath for 4 hr
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7acd2c29c698410fb68bd45e3c094565
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

Loading…