N-(2-amino-2-thioxoethyl)acetamide → 4-Acetyl-2-(acetylaminomethyl)thiazole

HRID 2379799Notes

Reaction equation

HRID 2379799 reaction equation
Br[CH2:2][C:3](=[O:7])[C:4](=O)[CH3:5].[C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])(=[S:10])[NH2:9]>CC(C)=O>[C:3]([C:4]1[N:9]=[C:8]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])[S:10][CH:5]=1)(=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 4435531N-(2-amino-2-thioxoethyl)acetamideHCID 109538801-Bromobutane-2,3-dione

Product 1

HCID 100129674-Acetyl-2-(acetylaminomethyl)thiazoleYield 92.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1-bromo-2,3-butanedione (47 g) and N-[(thiocarbamoyl)methyl]acetamide (30 g) in acetone (600 ml) was refluxed for 3 hours. The resulting precipitate was collected by filtration to afford 4-acetyl-2-(acetylaminomethyl)thiazole (41.8 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e1af559ed51a41ffb487c2e519ca1429
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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