p-Toluenesulfonic acid → HCID 20367281, compound

HRID 1605712Notes

Reaction equation

HRID 1605712 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 as 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. custommelted as 185°-186°
  11. customafter recrystallisation from ethanol

Sources & evidence

ORD record
ord-8728f065c59c420ab04a6590b212e1fa
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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