N-(2-amino-2-thioxoethyl)acetamide → 5-Acetyl-2-acetylaminomethylthiazole

HRID 2379797Notes

Reaction equation

HRID 2379797 reaction equation
Br[C:2]([C:5](=[O:7])[CH3:6])=[CH:3]O.[C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])(=[S:10])[NH2:9]>CC(C)=O>[C:5]([C:2]1[S:10][C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])=[N:9][CH:3]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 4435531N-(2-amino-2-thioxoethyl)acetamideHCID 573587893-Buten-2-one, 3-bromo-4-hydroxy-

Product 1

HCID 102418405-Acetyl-2-acetylaminomethylthiazoleYield 30.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-1-hydroxy-3-oxo-1-butene (9.61 g) and N-[(thiocarbamoyl)methyl]acetamide (7.70 g) in acetone (100 ml) was refluxed for one hour with stirring. The resulting precipitate was collected by filtration and chromatographed on silica gel eluting with a mixture of chloroform and methanol (20:1, V/V) to give 5-acetyl-2-(acetylaminomethyl)thiazole (3.48 g).

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationThe resulting precipitate was collected by filtration
  3. customchromatographed on silica gel eluting with a mixture of chloroform and methanol (20:1, V/V)

Sources & evidence

ORD record
ord-0b7702416fcc4b6aa4d1f897e1409d03
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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