Hydrogen Sulfide → 2,3-Diphenyl-5-o-chlorophenylthiophene

HRID 46660Notes

Reaction equation

HRID 46660 reaction equation
[C:1]1([C:7](=O)[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].S>C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[S:27][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[CH:9][C:8]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 14817Phosphorus sulfide (P2S5)HCID 53746567HCID 53746567, compound

Product 1

HCID 539258262,3-Diphenyl-5-o-chlorophenylthiopheneYield 67.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A 1-liter stainless steel stirred autoclave was charged with 33 g. (0.0946 mole) of 1,2-diphenyl-4-o-chlorophenylbutane-1,4-dione, 100 ml. of xylene, 20 g of phosphorus pentasulfide and 125 g of hydrogen sulfide. The autoclave was then heated at 160°-187° C. for three hours. The autoclave was cooled and vented. The residue was washed with ethanol and filtered off to give 17 g (51.8%) of crude product, m.p. 103°-107° C. Recrystallization from 20 ml of dioxane and 40 ml of ethanol gave 10.5 g (32%) of pure product, m.p. 117°-118° C.

Workup

  1. temperatureThe autoclave was then heated at 160°-187° C. for three hours
  2. temperatureThe autoclave was cooled
  3. washThe residue was washed with ethanol
  4. filtrationfiltered off
  5. customto give 17 g (51.8%) of crude product, m.p. 103°-107° C
  6. customRecrystallization from 20 ml of dioxane and 40 ml of ethanol

Sources & evidence

ORD record
ord-7753e8950ee947498c91a91e32258812
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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