N-[4-(Hydroxymethyl)-1,3-thiazol-2-YL]acetamide → N-(4-Formyl-1,3-thiazol-2-YL)acetamide
Reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.CO.[O-2].[O-2].[Mn+4]>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]=[O:11])[N:9]=1)(=[O:3])[CH3:2]Participants
5
Procedure
To a solution of 2-acetylamino-4-hydroxymethylthiazole (41 g) in a mixture of chloroform (2870 ml) and methanol (164 ml) was added manganese dioxide (410 g) with vigorous stirring for 1 hour and 20 minutes. The reaction mixture was filtered and the residue was added to a mixture of chloroform and ethanol (410 ml, 10:1 V/V). The mixture was heated with stirring and filtered. The residue was washed with a mixture of chloroform and ethanol (160 ml, 10:1 V/V). Every filtrates and washings were combined and evaporated to give 2-acetylamino-4formylthiazole (35.04 g).
Workup
- filtrationThe reaction mixture was filtered
- additionthe residue was added to a mixture of chloroform and ethanol (410 ml, 10:1 V/V)
- temperatureThe mixture was heated
- stirringwith stirring
- filtrationfiltered
- washThe residue was washed with a mixture of chloroform and ethanol (160 ml, 10:1 V/V)
- customevaporated
Sources & evidence
- ORD record
- ord-6df20fd506fd45ffa423d2307cbc027e
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04742057
Reaction notes
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