2-Methylbenzenesulfonic acid → 1-(3-Ethyl-5-methyl-4-isoxazolyl)ethanone 2-phenylhydrazone

HRID 905025Notes

Reaction equation

HRID 905025 reaction equation
[C:1]([C:4]1[C:5]([CH2:10][CH3:11])=[N:6][O:7][C:8]=1[CH3:9])(=O)[CH3:2].[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(O)C>[C:12]1([NH:18][N:19]=[C:1]([C:4]2[C:5]([CH2:10][CH3:11])=[N:6][O:7][C:8]=2[CH3:9])[CH3:2])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 7516PhenylhydrazineHCID 12720320HCID 12720320, compound

Product 1

HCID 731766431-(3-Ethyl-5-methyl-4-isoxazolyl)ethanone 2-phenylhydrazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 61.1 g. (0.4 mole) of 4-acetyl-3-ethyl-5-methyl-isoxazole, 39.4 ml. (0.4 mole) of phenyl hydrazine and 500 mg. toluenesulfonic acid in 400 ml. ethanol is stirred at room temperature for 48 hours. The resulting solid is filtered and washed with cold ether to give 1-(3-ethyl-5-methyl-4-isoxazolyl)-1-ethanone phenyl hydrazone; m.p. 72° to 75° C.

Workup

  1. additionA mixture of 61.1 g
  2. filtrationThe resulting solid is filtered
  3. washwashed with cold ether

Sources & evidence

ORD record
ord-eff9086a13bf445ab901c5d172f88de3
Source dataset
uspto-grants-1983_12
Patent number
US04421752

Reaction notes

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