p-Toluenesulfonic acid → HCID 20367191, compound

HRID 1605731Notes

Reaction equation

HRID 1605731 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][NH2:8])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C([O:17][C:18](=O)[CH:19]=[C:20]([NH2:24])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:24][C:20]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=2)[C:18](=[O:17])[CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 23334257{[4-Chloro-3-(trifluoromethyl)phenyl]methyl}hydrazine

Product 1

HCID 20367191HCID 20367191, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

67 g of 4-chloro-3-trifluoromethylbenzylhydrazine were added dropwise, under nitrogen, to a solution of 46.1 g of β-amino-β-ethoxyacrylic acid ethyl ester and 2 g of p-toluenesulphonic acid in 250 ml of ethanol. After stirring overnight, the solvent was distilled off in vacuo and the residue, which solidified, was filtered off and recrystallised from ethanol. The product was the compound identified above. Melting point: 132°, 25 g(30%).

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4525e44290d2430da1da1d641d8d2233
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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