p-Toluenesulfonic acid → HCID 20367255, compound

HRID 460894Notes

Reaction equation

HRID 460894 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 two 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 soltuion. 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°. 38 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 soltuion
  6. extractionThe alkaline solution was repeatedly extracted with ether
  7. customabove precipitated
  8. customAfter recrystallisation from ethanol

Sources & evidence

ORD record
ord-99df4863ba3e4bba91c9ed1a28a26b62
Source dataset
uspto-grants-1977_12
Patent number
US04061653

Reaction notes

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