Ethanol → HCID 178457164, compound

HRID 647139Notes

Reaction equation

HRID 647139 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:10][C:11](=[NH:15])OCC.[CH2:16](O)[CH3:17].N#[C:20][NH2:21].[CH2:22]([N:24](CC)CC)C>>[CH2:22]([NH:24][C:11](=[N:15][C:20]#[N:21])[CH:10]=[CH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[Cl:2])[CH2:16][CH3:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 9864CyanamideHCID 70532762HCID 70532762, compound

Product 1

HCID 178457164HCID 178457164, compound

Procedure

Step B--To the solution of 2.416 g. of ethyl 3-(o-chlorophenyl)-2-propenimidate hydrochloride in 9 ml. of ethanol, 0.01 g. of triethylamine and 0.42 g. of cyanamide are added successively. After stirring at room temperature for 1 hour, the solvent is removed under reduced pressure. To the residue, ethyl acetate and water are added. The ethyl acetate layer is washed with water and dried over Na2SO4. After removal of the solvent by distillation, the residue is dissolved in 10 ml. of ethanol. To this solution 3 ml. of n-propylamine are added and the resulting mixture is allowed to stand overnight. After removal of solvent, the product is washed with ethylacetate-n-hexane (1:1). Recrystallization from ethanol gives Compound 38 of the formula: ##STR38##

Workup

  1. customthe solvent is removed under reduced pressure
  2. additionTo the residue, ethyl acetate and water are added
  3. washThe ethyl acetate layer is washed with water
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvent
  6. distillationby distillation
  7. dissolutionthe residue is dissolved in 10 ml
  8. additionof n-propylamine are added
  9. waitto stand overnight
  10. customAfter removal of solvent
  11. washthe product is washed with ethylacetate-n-hexane (1:1)
  12. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-476237bf852e4408b9eecf567d7c8ade
Source dataset
uspto-grants-1983_10
Patent number
US04407816

Reaction notes

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