p-Toluenesulfonic acid → HCID 20367212, compound

HRID 460906Notes

Reaction equation

HRID 460906 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([NH2:10])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Br:33])[CH2:27][NH:28][NH2:29]>C(O)C>[NH2:10][C:6]1[NH:29][N:28]([CH2:27][C:26]2[CH:30]=[CH:31][C:32]([Br:33])=[C:24]([Br:23])[CH:25]=2)[C:4](=[O:3])[CH:5]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 23334356HCID 23334356, compound

Product 1

HCID 20367212HCID 20367212, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

12.2 g of β-amino-β-ethoxyacrylic acid ethyl ester together with 1 g of p-toluenesulphonic acid were dissolved in 200 ml of ethanol. A solution of 21.6 g of 3,4-dibromobenzylhydrazine in 50 ml of ethanol was added dropwise thereto, under nitrogen. After stirring overnight, the solvent was concentrated in vacuo and the compound identified above, which had separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 182°, 11 g (41%).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customhad separated out as a precipitate
  3. filtrationwas filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-78d51ae804234306ab504ed94e90aa11
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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