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

HRID 1246420Notes

Reaction equation

HRID 1246420 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-e25449450da046fc98a4239639a3803e
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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