Ethyl bromopyruvate → Ethyl 2-(3-hydroxy-4-methoxyanilino)-1,3-thiazole-4-carboxylate

HRID 1473981Notes

Reaction equation

HRID 1473981 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([NH2:13])=[S:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[S:12][CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 55276262HCID 55276262, compound

Product 1

HCID 53438568Ethyl 2-(3-hydroxy-4-methoxyanilino)-1,3-thiazole-4-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the general procedure for the synthesis of derivatives 6 and 7, a solution of 1-(3-hydroxy-4-methoxyphenyl)thiourea (150 mg, 0.76 mmol) and ethyl 3-bromopyruvate (0.095 mL, 0.76 mmol) in dry DMF (3.0 mL) was heated at 60° C. for 6 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 6/4) in 63% yield (139 mg).

Workup

  1. customfor the synthesis of derivatives 6 and 7

Sources & evidence

ORD record
ord-4d91efbfd2c3430589f6bd4a878bd3b6
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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