p-Toluenesulfonic acid → HCID 20367264, compound

HRID 460925Notes

Reaction equation

HRID 460925 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.[Cl:23][C:24]1[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:25]=1[CH2:26][NH:27][NH2:28]>C(O)C>[NH2:10][C:6]1[NH:28][N:27]([CH2:26][C:25]2[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:24]=2[Cl:23])[C:4](=[O:3])[CH:5]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 20367233[(2,3-Dichlorophenyl)methyl]hydrazine

Product 1

HCID 20367264HCID 20367264, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16.7 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1 g of p-toluenesulphonic acid were dissolved in 100 ml of ethanol and 20.2 g of 2,3-dichlorobenzylhydrazine were added. After standing overnight at room temperature, the precipitate which had formed was filtered off and dissolved in 2 N sodium hydroxide solution. The alkaline solution was again extracted with ether and subsequently slightly acidified with dilute acetic acid. Hereupon the compound identified above precipitated and after recrystallisation from ethanol the melting point was 161°-162° C. Yield: 11 g (40%).

Workup

  1. customthe precipitate which had formed
  2. filtrationwas filtered off
  3. dissolutiondissolved in 2 N sodium hydroxide solution
  4. extractionThe alkaline solution was again extracted with ether
  5. customabove precipitated
  6. customafter recrystallisation from ethanol the melting point was 161°-162° C

Sources & evidence

ORD record
ord-a6873184c9034a6f84046500e698afc1
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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