Hydrochloric Acid → 2-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide hydrochloride

HRID 2165415Notes

Reaction equation

HRID 2165415 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][CH:8]=1.[CH3:11][C:12](=[N:16][OH:17])[C:13](=O)[CH3:14].[ClH:18]>C(O)(=O)C>[ClH:18].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:13]([CH3:14])=[C:12]([CH3:11])[N+:16]=2[O-:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312444-MethoxybenzaldehydeHCID 63989692-Oxime 2,3-butanedione

Product 1

HCID 200640232-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 68.07 g of anisaldehyde, 50.5 g of 2,3-butanedione mono-oxime and 150 ml of acetic acid was saturated with hydrogen chloride gas and the mixture was allowed to stand at room temperature for 3 hours. The solid product was collected and recrystallized from methanol to give 2-(4-methoxyphenyl)-4,5-dimethyloxazole N-oxide hydrochloride, m.p. 194°-196° C. The latter was converted to the free base for use in the next reaction by treatment with sodium bicarbonate solution.

Workup

  1. customThe solid product was collected
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2bcec526929f41eb9074f46939f94257
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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