Ethyl bromopyruvate → HCID 72210847, compound

HRID 1473980Notes

Reaction equation

HRID 1473980 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 55276261HCID 55276261, compound

Product 1

HCID 72210847HCID 72210847, compoundYield 65%

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-methylphenyl)thiourea (100 mg, 0.59 mmol) and ethyl 3-bromopyruvate (0.074 mL, 0.59 mmol) in dry DMF (2.4 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 65% yield (105 mg).

Workup

  1. customfor the synthesis of derivatives 6 and 7

Sources & evidence

ORD record
ord-83094406d71d4504b83c1e67b9b544c4
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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