Thiourea → Ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate

HRID 2117908Notes

Reaction equation

HRID 2117908 reaction equation
Br[CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[NH2:20][C:18]1[S:19][C:2]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:17]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 10755525Ethyl 3-bromo-2-oxo-4-phenylbutanoate

Product 1

HCID 12603729Ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylateYield 15.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-bromo-2-oxo-4-phenylbutanoate (5.8 g) was dissolved in EtOH (110 ml), and then thiourea (3.1 g) was added to the solution. The reaction mixture was refluxed for 2 hours under N2 atmosphere. The cooled reaction mixture was evaporated in vacuo. The residual solid was suspended (pH=8) in saturated NaHCO3 and water. The solid was collected by filtration, and purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent to give ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate (808.2 mg) as a yellow wax.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours under N2 atmosphere
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo
  4. filtrationThe solid was collected by filtration
  5. custompurified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent

Sources & evidence

ORD record
ord-e0ea201cdc9a46b79348f3006c5ad841
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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