Ethyl thiooxamate → Ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate

HRID 517552

Reaction equation

HRID 517552 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH:10]([CH3:21])[C:11](=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1>CN(C=O)C.CCOC(C)=O>[Br:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C:11]1[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][C:10]=1[CH3:21]

Participants

5

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 867114923-Bromo-1-(3-bromophenyl)butan-2-one

Product 1

HCID 86711493Ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 2-amino-2-thioxoacetate (50.9 mg, 0.38 mmol) and 3-bromo-1-(3-bromophenyl)butan-2-one (0.38 mmol, crude from previous step) in DMF (2 mL) was stirred at 70° C. for 12 h. The mixture was diluted with EtOAc and washed with H2O. The organic layer was concentrated, and purified by silica gel column chromatography(0-50% EtOAc/Hexane) to yield a yellowish solid (71 mg, 55% over 2 steps). MS (ES+) C14H14BrNO2S requires: 339, 341 found: 340, 342 [M+H]+(1:1).

Workup

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel column chromatography(0-50% EtOAc/Hexane)
  4. customto yield a yellowish solid (71 mg, 55% over 2 steps)

Sources & evidence

ORD record
ord-5e08d89a8e144122b3b56f9f5521f41a
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Linked notes

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