p-Toluenesulfonic acid → HCID 20367265, compound

HRID 1605729Notes

Reaction equation

HRID 1605729 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][NH:7][NH2:8])([O-:3])=[O:2].C([O:15][C:16](=O)[CH:17]=[C:18]([NH2:22])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:22][C:18]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[C:16](=[O:15])[CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367201[(2-Nitrophenyl)methyl]hydrazine

Product 1

HCID 20367265HCID 20367265, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

47.8 g of o-nitrobenzylhydrazine were added dropwise, under nitrogen, to a solution of 45.5 g of β-amino-β-ethoxyacrylic acid ethyl ester and a pinch of p-toluenesulphonic acid in 200 ml of ethanol. After standing overnight, the solvent was distilled off in vacuo and the residue was treated with a 2:1 mixture of ether and ethanol. The compound identified above which thereupon precipitated was filtered off and recrystallised from ethanol. Melting point: 190°, 23 g (34%).

Workup

  1. distillationthe solvent was distilled off in vacuo
  2. additionthe residue was treated with a 2:1 mixture of ether and ethanol
  3. customthereupon precipitated
  4. filtrationwas filtered off
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-973c8ae687f04c9cbfff0f69709b4f37
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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