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

HRID 2117831Notes

Reaction equation

HRID 2117831 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1>CO.C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1)=[O:1]

Participants

5

Reactant 1

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

Product 1

HCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamideYield 72.6%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

N-(4-(Hydroxymethyl)-1,3-thiazol-2-yl)acetamide (2.8 g) was dissolved in methanol (10 ml) and chloroform (200 ml). Then manganese (IV) oxide (28.3 g) was added to the solution under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 7 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo. The resulting solid was washed with ethyl ether to give N-(4-formyl-1,3-thiazol-2-yl)acetamide (2.01 g) as an off-white solid.

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. washThe resulting solid was washed with ethyl ether

Sources & evidence

ORD record
ord-807d227957db470eba176f039646789a
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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