Methanol → N-[4-(Hydroxymethyl)-1,3-thiazol-2-YL]acetamide

HRID 1252060Notes

Reaction equation

HRID 1252060 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][O:11]C(=O)C)[N:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO>O>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 14931747(2-Acetamido-1,3-thiazol-4-yl)methyl acetate

Product 1

HCID 14931748N-[4-(Hydroxymethyl)-1,3-thiazol-2-YL]acetamideYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mass (m/e): 214 (M30) . (2) A mixture of 2-acetylamino-4-acetoxymethylthiazole (72 g), potassium carbonate (23.2 g), methanol (1.1 l) and water (0.1 l) was stirred for 3 hours and 20 minutes at ambient temperature. An insoluble material was filtered off and the filtrate was neutralized with 2N hydrochloric acid and evaporated. To the residue was added a mixture of chloroform and methanol (100 ml, 1:1 V/V) and the mixture was heated. An insoluble material was filtered off and the filtrate was concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V) to give 2-acetylamino-4-hydroxymethylthiazole (41.11 g).

Workup

  1. filtrationAn insoluble material was filtered off
  2. customevaporated
  3. additionTo the residue was added
  4. additiona mixture of chloroform and methanol (100 ml, 1:1 V/V)
  5. temperaturethe mixture was heated
  6. filtrationAn insoluble material was filtered off
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V)

Sources & evidence

ORD record
ord-4c7a82f635a342cfa02633bb9fa5d2cb
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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