Hydrogen Sulfide → 2,3-Diphenyl-5-p-methoxyphenylthiophene

HRID 46662Notes

Reaction equation

HRID 46662 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]([O:18][CH3:19])=[CH:14][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]([O:18][CH3:19])=[CH:14][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 Sulfide2×HCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 27330391,2-Diphenyl-4-p-methoxyphenylbutane-1,4-dione

Product 1

HCID 540912942,3-Diphenyl-5-p-methoxyphenylthiopheneYield 142.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1-liter steel autoclave fitted with a mechanical stirrer, a thermometer and a pressure gauge were placed 32 g (0.09 mole) of 1,2-diphenyl-4-p-methoxyphenylbutane-1,4-dione, 100 ml of xylene, 20 g (0.045 mole) of phosphorus pentasulfide and 130 g of hydrogen sulfide. The mixture was stirred and heated 3 hours at 157°-162° C. (1190-1220 psig). The vessel was cooled and the hydrogen sulfide vented into an aqueous sodium hydroxide trap. The semisolid residue was stirred with 150 ml of absolute ethanol. Filtration gave 23 g (72%) of crude product, m.p. 130°-132° C. and a second crop of 3.7 g (11.6%) m.p. 124°-126° C. The two crops were combined and recrystallized from a mixture of 30 ml of dioxane and 60 ml of absolute ethanol to give 22 g (69%) of pure product m.p. 133°-134° C.

Workup

  1. temperatureheated 3 hours at 157°-162° C. (1190-1220 psig)
  2. temperatureThe vessel was cooled
  3. filtrationFiltration
  4. customgave 23 g (72%) of crude product, m.p. 130°-132° C.
  5. customrecrystallized from a mixture of 30 ml of dioxane and 60 ml of absolute ethanol

Sources & evidence

ORD record
ord-3d4393c5c73f41ff80a02d1f48faa88f
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

Loading…