p-Toluenesulfonic acid → HCID 20367303, compound

HRID 460905Notes

Reaction equation

HRID 460905 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[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[C:2]([F:1])=[CH:10][CH:9]=[C:8]([Cl:11])[CH:7]=2)[C:15](=[O:14])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 54490407[(5-Chloro-2-fluorophenyl)methyl]hydrazine

Product 1

HCID 20367303HCID 20367303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.6 g of 2-fluoro-5-chlorobenzylhydrazine were added dropwise under nitrogen to a solution of 19.8 g of β-amino-β-ethoxyacrylic acid ethyl ester and 0.5 g of p-toluenesulphonic acid in 100 ml of ethanol, in the course of which the temperature rose from 20° to 30°. After stirring for two hours, the mixture was left to stand overnight and the compound identified above, which had separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 160°, 17 g (57%).

Workup

  1. customrose from 20° to 30°
  2. waitthe mixture was left
  3. waitto stand overnight
  4. customhad separated out as a precipitate
  5. filtrationwas filtered off
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-cf8694e9197843108ad4c8cb36818253
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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