Ammonium Hydroxide → 4-Methyloxazole-5-carboxamide

HRID 1672023

Reaction equation

HRID 1672023 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]([O:9]CC)=O.[OH-].[NH4+:13]>>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]([NH2:13])=[O:9]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 88558Ethyl 4-methyloxazole-5-carboxylate

Product 1

HCID 785814-Methyloxazole-5-carboxamide

Procedure

A mixture of ethyl 4-methyloxazole-5-carboxylate (7.8 g, 50 mmoles) and ammonium hydroxide in a seal tube was stirred at rt for 12 hours. After completion of the reaction, solid was filtered and washed with water. The aqueous was extracted with ethyl acetate. The organic extract was dried and concentrated and combined with the filtered solid. Yield: 4.1 g (47%) 1H NMR (400 MHz, CDCl3): δ 2.38 (s, 3H), 7.92 (s, 1H). LCMS: (ES+) m/z=126.7 (M)+

Workup

  1. customAfter completion of the reaction, solid
  2. filtrationwas filtered
  3. washwashed with water
  4. extractionThe aqueous was extracted with ethyl acetate
  5. extractionThe organic extract
  6. customwas dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c938aa01827d4e4984ffa818bb4f2b21
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Linked notes

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