p-Toluenesulfonic acid → HCID 20367281, compound

HRID 617027Notes

Reaction equation

HRID 617027 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][NH:12][NH2:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:18][C:19](=O)[CH:20]=[C:21]([NH2:25])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:25][C:21]1[NH:13][N:12]([CH2:11][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[C:19](=[O:18])[CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 53236BIPHENYL-4-YLMETHYL-HYDRAZINEHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl ester

Product 1

HCID 20367281HCID 20367281, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 29 g of 4-phenylbenzylhydrazine in 60 ml of ethanol was added dropwise, under nitrogen, to a solution of 23.4 g (0.147 mol) of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid in 100 ml of ethanol. During addition the temperature rose from 22° to 32° C. After standing overnight, the reaction solution was concentrated in vacuo, the precipitate which separated out was dissolved in 2 N sodium hydroxide solution and the alkaline solution was repeatedly extracted with ether. Addition of dilute acetic acid until the mixture reacted weakly acid yielded the compound identified above, which melted at 185°-186° after recrystallisation from ethanol. 13 g (33%).

Workup

  1. additionDuring addition the temperature
  2. customrose from 22° to 32° C
  3. concentrationthe reaction solution was concentrated in vacuo
  4. customthe precipitate which separated out
  5. dissolutionwas dissolved in 2 N sodium hydroxide solution
  6. extractionthe alkaline solution was repeatedly extracted with ether
  7. additionAddition of dilute acetic acid until the mixture
  8. customreacted weakly acid
  9. customyielded the compound
  10. customafter recrystallisation from ethanol

Sources & evidence

ORD record
ord-8fa1924c3f754670bdb35e7c7fb176c7
Source dataset
uspto-grants-1978_02
Patent number
US04076943

Reaction notes

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