Phosphorus sulfide (P2S5) → 2H-Pyran-2-thione, 4,6-diphenyl-

HRID 1165285Notes

Reaction equation

HRID 1165285 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9](=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>C1C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9](=[S:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 2966854,6-diphenyl-2H-pyran-2-one

Product 1

HCID 1861062H-Pyran-2-thione, 4,6-diphenyl-Yield 134.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under an inert atmosphere, 2.1 g of the product of Step A 45 ml of benzene and 7.5 g of phosphorus pentasulfide were mixed together and refluxed under inert atmosphere for 5 hours. Then the supernatant solution was decanted hot and concentrated to dryness by distilling under reduced pressure. This operation was repeated hot on the reaction medium four times, each time with 30 ml of benzene. The concentrates were put together and dried under a good vacuum to obtain 3 g of product which was chromatographed on silica and eluted with methylene chloride to obtain 2 g of the product sought melting at 122°-123° C.

Workup

  1. temperaturerefluxed under inert atmosphere for 5 hours
  2. customThen the supernatant solution was decanted hot
  3. concentrationconcentrated to dryness
  4. distillationby distilling under reduced pressure
  5. customdried under a good vacuum

Sources & evidence

ORD record
ord-4de36a03eb69437e9c456d72aecbb8af
Source dataset
uspto-grants-1990_03
Patent number
US04908359

Reaction notes

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