p-Toluenesulfonic acid → HCID 20367247, compound

HRID 1605724Notes

Reaction equation

HRID 1605724 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][NH:10][NH2:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].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:11][N:10]([CH2:9][C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:13][CH:12]=2)[C:17](=[O:16])[CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 16771957[(4-tert-Butylphenyl)methyl]hydrazine

Product 1

HCID 20367247HCID 20367247, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.6 g of p-tert.butylbenzylhydrazine were added dropwise, under nitrogen, to a solution of 22 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid in 100 ml of ethanol, in the course of which the temperature rose from 24° to 30°C. After stirring overn the solvent was distilled off in vacuo and the oily residue solidified after addition of 50 ml of petroleum ether. The compound identified above was filtered off and recrystallised from ethanol. Melting poing: 126°, 8 g (24%).

Workup

  1. customrose from 24° to 30°C
  2. distillationwas distilled off in vacuo
  3. additionafter addition of 50 ml of petroleum ether
  4. filtrationabove was filtered off
  5. customrecrystallised from ethanol
  6. custom126°, 8 g (24%)

Sources & evidence

ORD record
ord-c3f0c98f28d74a45b4550c19096b5e2b
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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