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

HRID 1252061
Notes
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Reaction equation

HRID 1252061 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 86.5%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

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

  1. filtrationThe reaction mixture was filtered
  2. additionthe residue was added to a mixture of chloroform and ethanol (410 ml, 10:1 V/V)
  3. temperatureThe mixture was heated
  4. stirringwith stirring
  5. filtrationfiltered
  6. washThe residue was washed with a mixture of chloroform and ethanol (160 ml, 10:1 V/V)
  7. customevaporated

Sources & evidence

ORD record
ord-6df20fd506fd45ffa423d2307cbc027e
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04742057

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes