Hydrazine hydrate (1:1) → HCID 22911709, compound

HRID 1378448Notes

Reaction equation

HRID 1378448 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([O:17]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>CO.O>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([NH:20][NH2:21])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14255313HCID 14255313, compound

Product 1

HCID 22911709HCID 22911709, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl (2-phenoxyphenyl)acetate (6.0 g) in methanol (100 ml) was added dropwise with stirring to hydrazine hydrate (12 ml). The resulting mixture was stirred for 2 hours, then diluted with water and extracted with ether. The extracts were washed with water, dried and concentrated to give almost pure (2-phenoxyphenyl)acetohydrazide (5.8 g, 96% yield) as a waxy solid with amp of about 65° C., 1H NMR (CDCl3): delta 3.60 (2H,s) ppm. Concentrated sulphuric acid (4 drops) was added to a mixture of this hydrazide and triethyl orthoformate (20 ml) and the resulting mixture was heated at 90° C. for one hour. After cooling, water was added to the mixture and it was extracted with ether. The extracts were washed, dried, concentrated and chromatographed using increasing proportions (up to 50%) of ethyl acetate in hexane as eluant to give 2-(2-phenoxyphenylmethyl)oxa-1,3,4-diazole (3.14 g, 52% yield) as a yellow oil, IH NMR (CDCl3): delta 4.31 (2H,s) and 8.28 (1H,s) ppm.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a40d30f9c34d4d1eabc7f570739b6389
Source dataset
uspto-grants-1997_09
Patent number
US05668160

Reaction notes

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