Dimethylformamide → 2-Amino-4-formylthiazole-5-carboxylic acid methyl ester

HRID 908632Notes

Reaction equation

HRID 908632 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH2:11][OH:12])=[O:4].CN(C)C=O>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH:11]=[O:12])=[O:4]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 12308572Methyl 2-amino-4-(hydroxymethyl)thiazole-5-carboxylate

Product 1

HCID 597038082-Amino-4-formylthiazole-5-carboxylic acid methyl esterYield 89.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound (1.35 g) obtained in Step 3 in 1,4-dioxane (68 ml)/N,N-dimethylformamide (13 ml) was added manganese dioxide (3.68 g) at room temperature and the mixture was stirred at room temperature for 40 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (1.20 g).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b079d13d866d4fc7b21620b8185b1d05
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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