p-Toluenesulfonic acid → 3-Amino-4-n-butyl-1-(3,4-dichlorobenzyl)-pyrazol-5-one

HRID 1605167Notes

Reaction equation

HRID 1605167 reaction equation
C([O:3][C:4](=O)[C:5]([CH2:11][CH2:12][CH2:13][CH3:14])=[C:6]([NH2:10])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:31][NH:32][NH2:33]>C(O)C>[NH2:10][C:6]1[NH:33][N:32]([CH2:31][C:30]2[CH:34]=[CH:35][C:36]([Cl:37])=[C:28]([Cl:27])[CH:29]=2)[C:4](=[O:3])[C:5]=1[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 20495842(3,4-Dichlorobenzyl)hydrazineHCID 86733217alpha-n-Butyl-beta-amino-beta-ethoxyacrylic acid ethyl ester

Product 1

HCID 233342753-Amino-4-n-butyl-1-(3,4-dichlorobenzyl)-pyrazol-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 41.1 g α-n-butyl-β-amino-β-ethoxyacrylic acid ethyl ester and a spatula tipfull of p-toluenesulphonic acid in 100 ml ethanol were added dropwise, under nitrogen, 36.5 g 3,4-dichlorobenzylhydrazine. After the mixture had been stirred afterwards for two hours, it was left to stand overnight. The solvent was distilled off, a mixture of ether/petroleum ether (1:1) was added to the residue; the product crystallized through.

Workup

  1. waitit was left
  2. waitto stand overnight
  3. distillationThe solvent was distilled off
  4. additiona mixture of ether/petroleum ether (1:1)
  5. additionwas added to the residue
  6. customthe product crystallized through

Sources & evidence

ORD record
ord-4be1638ee22d48ddb30fa7ab9234a43d
Source dataset
uspto-grants-1976_04
Patent number
US03949083

Reaction notes

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