p-Toluenesulfonic acid → HCID 20367290, compound

HRID 460900Notes

Reaction equation

HRID 460900 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][NH:5][NH2:6].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:6][N:5]([CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[CH3:1])[C:14](=[O:13])[CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 12883868[(2-Methylphenyl)methyl]hydrazine

Product 1

HCID 20367290HCID 20367290, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

27.5 g of o-methylbenzylhydrazine, dissolved in 100 ml of ethanol, were added dropwise at room temperature to a solution of 32 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1.5 g of p-toluenesulphonic acid in 300 ml of ethanol. After standing overnight, the reaction solution was concentrated in vacuo and the compound identified above, which separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 138°, 15 g (37%).

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. customseparated out as a precipitate
  3. filtrationwas filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-0371903a3ced443896b22cb00f9d2c11
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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