p-Toluenesulfonic acid → HCID 20367301, compound

HRID 617034Notes

Reaction equation

HRID 617034 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][NH2:8])=[CH:4][CH:3]=1.C([O:13][C:14](=O)[CH:15]=[C:16]([NH2:20])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:20][C:16]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[C:14](=[O:13])[CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367299[(4-Iodophenyl)methyl]hydrazine

Product 1

HCID 20367301HCID 20367301, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 25.5 g of p-iodobenzylhydrazine in 100 ml of ethanol was added dropwise, under nitrogen, to a solution of 16.2 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid in 250 ml of ethanol. After stirring overnight, the solvent was distilled off in vacuo and the compound identified above was obtained as a residue and recrystallised from ethanol. Melting point: 158°, 15 g (47%).

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. customabove was obtained as a residue
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-2278c3fbe4f34b79a2ed9fa7341cbd9f
Source dataset
uspto-grants-1978_02
Patent number
US04076943

Reaction notes

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