Pyridine → HCID 54495913, compound

HRID 892621Notes

Reaction equation

HRID 892621 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]=[CH:7][C:8]([NH:10][CH:11]2[CH2:18][CH2:17][CH2:16]NC(=O)[CH2:12]2)=O)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].C(=O)([O-])O.[Na+].[N:40]1[CH:45]=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]2[S:22][C:12]3[NH:40][CH2:45][CH2:16][CH2:17][CH2:18][C:11]=3[N:10]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 53775811HCID 53775811, compound

Product 1

HCID 54495913HCID 54495913, compound

Procedure

3-(4-Chlorocinnamoyl)amino-ε-caprolactam (11.0 g) and phosphorus pentasulfide (8.37 g) were added to 500 ml of pyridine, and the whole was refluxed for 1.5 hrs. After cooling, the reaction mixture was added to a sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with water, dried and the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography on silica gel, and recrystallized from cyclohexane to give the title compound as crystals, m.p. 188°-189° (yield 6.28 g, 57% of theory).

Workup

  1. temperaturethe whole was refluxed for 1.5 hrs
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by a column chromatography on silica gel
  8. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-d7e7e18ceffc4a27be6787194df3d10c
Source dataset
uspto-grants-1992_06
Patent number
US05118806

Reaction notes

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