p-Toluenesulfonic acid → HCID 20367255, compound

HRID 1605710Notes

Reaction equation

HRID 1605710 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[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[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]=[C:30]([Cl:34])[C:31]([Cl:33])=[CH:32][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 20367250HCID 20367250, compound

Product 1

HCID 20367255HCID 20367255, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

54.7 g of β-amino-β-ethoxyacrylic acid ethyl ester and 2 g of p-toluenesulphonic acid were dissolved in 400 ml of ethanol. A solution of 77.6 g of 2,4,5-trichlorobenzylhydrazine in 200 ml of ethanol was added dropwise thereto, under nitrogen. After stirring for a further 2 hours, the mixture was left to stand overnight and the precipitate which had separated out was filtered off and dissolved in 2 N sodium hydroxide solution. The alkaline solution was repeatedly extracted with ether and subsequently slightly acidified with dilute acetic acid, whereupon the compound identified above precipitated. After recrystallisation from ethanol, this product melted at 195°-196°. 35 g (38%).

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. customthe precipitate which had separated out
  4. filtrationwas filtered off
  5. dissolutiondissolved in 2 N sodium hydroxide solution
  6. extractionThe alkaline solution was repeatedly extracted with ether
  7. customabove precipitated
  8. customAfter recrystallisation from ethanol

Sources & evidence

ORD record
ord-918c2cf347254cd2a8315a0e152625d4
Source dataset
uspto-grants-1976_04
Patent number
US03950528

Reaction notes

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