Hydrogen Sulfide → 5-(3,4-Dichlorophenyl)-2,3-diphenylthiophene

HRID 46661Notes

Reaction equation

HRID 46661 reaction equation
[C:1]1([C:7](=O)[CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C(C)=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:36].S>C(O)C>[C:1]1([C:7]2[S:36][C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=3)=[CH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 124882441,2-Diphenyl-4-(3,4-dichlorophenyl)butane-1,4-dione

Product 1

HCID 203866215-(3,4-Dichlorophenyl)-2,3-diphenylthiopheneYield 177.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1-liter stainless steel autoclave equipped with electrically-driven stirrer were placed 38.3 g. (0.100 mole) of 1,2-diphenyl-4-(3,4-dichlorophenyl)butane-1,4-dione, 100 ml of xylene, 20 g of phosphorus pentasulfide and 140 g of hydrogen sulfide. The reactor was heated for three hours at 160°-164° C. The crude product remaining after cooling and venting the reactor was stirred with ethanol. Filtration gave 30.5 g (80%) of solid m.p. 101°-103° C. Recrystallization from 30 ml of dioxane and 60 ml of ethanol gave 22.5 g (59%) of pure product, m.p. 106.2°-107.8° C.

Workup

  1. temperatureThe reactor was heated for three hours at 160°-164° C
  2. temperatureafter cooling
  3. filtrationFiltration

Sources & evidence

ORD record
ord-2f76414035bb4e89af3691c46890b0d9
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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