p-Toluenesulfonic acid → HCID 20367208, compound

HRID 617045Notes

Reaction equation

HRID 617045 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][NH2:8])=[CH:4][C:3]=1[O:11][CH2:12][CH3:13].C([O:16][C:17](=O)[CH:18]=[C:19]([NH2:23])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:23][C:19]1[NH:8][N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([O:11][CH2:12][CH3:13])[CH:4]=2)[C:17](=[O:16])[CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367320HCID 20367320, compound

Product 1

HCID 20367208HCID 20367208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

45.5 g of 4-chloro-3-ethoxybenzylhydrazine were added, under nitrogen, to a solution of 35 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid in 200 ml of ethanol. After stirring overnight, the compound identified above, which had separated out as a precipitate, was filtered off and recrystallised from ethanol. Melting point: 143°, 15.2 g (26%).

Workup

  1. customhad separated out as a precipitate
  2. filtrationwas filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-5f2a503bb3e24a24affd70970bd486d7
Source dataset
uspto-grants-1978_02
Patent number
US04076943

Reaction notes

Loading…