p-Toluenesulfonic acid → HCID 20367222, compound

HRID 1605728Notes

Reaction equation

HRID 1605728 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][NH2:8])=[CH:4][C:3]=1[O:11][CH3:12].C([O:15][C:16](=O)[CH:17]=[C:18]([NH2:22])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:22][C:18]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[C:16](=[O:15])[CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367192HCID 20367192, compound

Product 1

HCID 20367222HCID 20367222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

59 g of 4-chloro-3-methoxybenzylhydrazine were added dropwise, under nitrogen, to a solution of 50.5 g of β-amino-βethoxyacrylic acid ethyl ester and 1.5 g of p-toluenesulphonic acid in 250 ml of ethanol. After standing overnight, the compound identified above, which had separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 148°, 30 g. (38%).

Workup

  1. customhad separated out as a precipitate
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-cf8eab68da124056aca92028a439e0e8
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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