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

HRID 2117830Notes

Reaction equation

HRID 2117830 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[S:9][CH:10]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[S:9][CH:10]=1

Participants

4

Reactant 2

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

Product 1

HCID 14931748N-[4-(Hydroxymethyl)-1,3-thiazol-2-YL]acetamideYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2-(acetylamino)-1,3-thiazol-4-yl)methyl acetate (46 g) and potassium carbonate (30 g) in methanol (640 ml) was stirred for 3 hours at ambient temperature. The reaction mixture was concentrated in vacuo. The residue was diluted with chloroform, and the insoluble material was filtered off. The resulting solution was purified by flash column chromatography on silica-gel with methanol/chloroform (1/99). The resulted solid was collected by filtration with isopropyl ether to give N-(4-(hydroxymethyl)-1,3-thiazol-2-yl)acetamide (35 g) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with chloroform
  3. filtrationthe insoluble material was filtered off
  4. customThe resulting solution was purified by flash column chromatography on silica-gel with methanol/chloroform (1/99)
  5. filtrationThe resulted solid was collected by filtration with isopropyl ether

Sources & evidence

ORD record
ord-2542f15029d44bf5841df3453f9caa84
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

Loading…