p-Toluenesulfonic acid → HCID 20367322, compound

HRID 460901Notes

Reaction equation

HRID 460901 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 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°, 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-2bee44edf3834bf3a5f2005a4d656082
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

Loading…