Thiourea → 2-Amino-4-(2-chloro-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667660Notes

Reaction equation

HRID 1667660 reaction equation
Br[CH:2]([C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=O)[C:3]([NH2:5])=[O:4].[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[NH2:18][C:16]1[S:17][C:2]([C:3]([NH2:5])=[O:4])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86642797HCID 86642797, compound

Product 1

HCID 593753542-Amino-4-(2-chloro-phenyl)-thiazole-5-carboxylic acid amideYield 33.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.33 g (8.43 mmole) of 2-bromo-3-(2-chloro-phenyl)-3-oxo-propionamide, 0.77 g (10.11 mmole) of thiourea and 20 mL of ethanol was stirred at room temperature for 18 hours. The mixture was then concentrated under reduced pressure. The residue was purified by chromatography on C18 reverse phase silica gel, eluting with acetonitrile-water (gradient 0:100-50:50) to give 0.72 g of 2-amino-4-(2-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.20).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customThe residue was purified by chromatography on C18 reverse phase silica gel
  3. washeluting with acetonitrile-water (gradient 0:100-50:50)

Sources & evidence

ORD record
ord-cbedf6b88cd440118709d4957963de95
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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