p-Toluenesulfonic acid → HCID 20367199, compound

HRID 1605733Notes

Reaction equation

HRID 1605733 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][NH:7][NH2:8])[CH3:2].C([O:14][C:15](=O)[CH:16]=[C:17]([NH2:21])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:21][C:17]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[C:15](=[O:14])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 23334262HCID 23334262, compound

Product 1

HCID 20367199HCID 20367199, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.2 g of 3-ethylbenzylhydrazine were added dropwise to a solution of 15.1 g of β-amino-β-ethoxyacrylic acid ethyl ester and a pinch of p-toluenesulphonic acid in 80 ml of ethanol, in the course of which the temperature rose from 22°to 30°. After stirring overnight, the solvent was distilled off in vacuo and the solid residue was recrystallised from ethanol. The product was the compound identified above. Melting point: 73°, 5 g (24%).

Workup

  1. customrose from 22°to 30°
  2. distillationthe solvent was distilled off in vacuo
  3. customthe solid residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-68cf32ef041c48a4bc3e8a7e9870cb1e
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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