Phosphorus sulfide (P2S5) → HCID 13368794, compound

HRID 483095Notes

Reaction equation

HRID 483095 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([CH2:6][CH:7]3[CH2:11][C:10](=O)[NH:9][CH:8]32)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([CH2:6][CH:7]3[CH2:11][C:10](=[S:16])[NH:9][CH:8]32)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 13368797HCID 13368797, compound

Product 1

HCID 13368794HCID 13368794, compoundYield 225.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4.2 g of 7-chloro-1,2,3,3a,4,8b-hexahydro-indeno[1,2-b]pyrrol-2-one in 100 ml of pyridine is added 2.2 g of diphosphorus pentasulfide, and the mixture is stirred at 90° C. for 1 hour. The reaction mixture is then cooled, poured into ice-cold water and extracted with ethyl acetate. The extract is washed with water and dried over sodium sulfate, and the solvent is distilled off. The residual oil is chromatographed over silica gel with chloroform eluant. The purified product is crystallized with isopropyl ether and recrystallized from the same solvent to give 2.5 g of 7-chloro-1,2,3,3a,4,8b-hexahydro-indeno[1,2-b]pyrrol-2-thione, melting at 225°-227° C.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. additionpoured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe residual oil is chromatographed over silica gel with chloroform eluant
  8. customThe purified product is crystallized with isopropyl ether
  9. customrecrystallized from the same solvent

Sources & evidence

ORD record
ord-17f0cb4124fe4f96ab93aa4dd0471537
Source dataset
uspto-grants-1986_03
Patent number
US04578397

Reaction notes

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