p-Toluenesulfonic acid → HCID 20367252, compound

HRID 460916Notes

Reaction equation

HRID 460916 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][NH:6][NH2:7].C([O:16][C:17](=O)[CH:18]=[C:19]([NH2:23])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:23][C:19]1[NH:7][N:6]([CH2:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:12])([F:13])[F:1])[C:17](=[O:16])[CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367279{[2-(Trifluoromethyl)phenyl]methyl}hydrazine

Product 1

HCID 20367252HCID 20367252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

46 g of 2-trifluoromethylbenzylhydrazine were added dropwise, under nitrogen, to a solution of 38.2 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 was recrystallized from ethanol. The product was the compound identified above. Melting point: 184°, 22 g (34%).

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cb261811cccd43a5bcb681a1d4b56aa2
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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