p-Toluenesulfonic acid → 3-Amino-1-(3-bromo-4-chlorobenzyl)-pyrazol-5-one

HRID 460892

Reaction equation

HRID 460892 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([NH2:10])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:27][NH:28][NH2:29]>C(O)C>[NH2:10][C:6]1[NH:29][N:28]([CH2:27][C:26]2[CH:30]=[CH:31][C:32]([Cl:33])=[C:24]([Br:23])[CH:25]=2)[C:4](=[O:3])[CH:5]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 233343553-Bromo-4-chlorobenzylhydrazine

Product 1

HCID 203673153-Amino-1-(3-bromo-4-chlorobenzyl)-pyrazol-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

49 g of β-amino-β-ethoxyacrylic acid ethyl ester and 2 g of p-toluenesulphonic acid were dissolved in 225 ml of ethanol and 72 g of 3 -bromo-4-chlorobenzylhydrazine were added under nitrogen. After standing overnight, the compound identified above had settled out as a precipitate and was filtered off and recrystallised twice from ethanol. Melting point: 171°-172° C, 40 g (43%).

Workup

  1. filtrationwas filtered off
  2. customrecrystallised twice from ethanol

Sources & evidence

ORD record
ord-dc2f9e3c43324419b09926dd65c45197
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Linked notes

Loading…