p-Toluenesulfonic acid → HCID 20367296, compound

HRID 1605726Notes

Reaction equation

HRID 1605726 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[CH2:4][NH:5][NH2:6].C([O:14][C:15](=O)[CH:16]=[C:17]([NH2:21])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:21][C:17]1[NH:6][N:5]([CH2:4][C:3]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=2[Cl:1])[C:15](=[O:14])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 16773950[(2-Chloro-4-fluorophenyl)methyl]hydrazine

Product 1

HCID 20367296HCID 20367296, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

53.8 g of 2-chloro-4-fluorobenzylhydrazine were added dropwise, under nitrogen, to a solution of 49.2 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid in 250 ml of ethanol, in the course of which the temperature rose from 22° to 32°C. After standing overnight, the compound identified above, which had separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 192°, 25 g (34%).

Workup

  1. customrose from 22° to 32°C
  2. customhad separated out as a precipitate
  3. filtrationwas filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-41d4880c8303496d9e09ce3747472c28
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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