p-Toluenesulfonic acid → HCID 20367322, compound

HRID 1605717Notes

Reaction equation

HRID 1605717 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][CH:32]=1)[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][CH:32]=[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 16776578[(3-Bromophenyl)methyl]hydrazine

Product 1

HCID 20367322HCID 20367322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.5 g of β-amino-β-ethoxyacrylic acid ethyl ester together with 1.5 g of p-toluenesulphonic acid were dissolved in 200 ml of ethanol. 26 g of m-bromobenzylhydrazine were added dropwise to this solution, under nitrogen. After stirring for 2 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°, 12 g (35%).

Workup

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

Sources & evidence

ORD record
ord-6ad3cbd628d842a98f4d9e33271691c7
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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