Hydrogen Sulfide → 2,3-Diphenyl-5-m-anisylthiophene

HRID 46657Notes

Reaction equation

HRID 46657 reaction equation
[C:1]1([C:7](=O)[CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:29].S.[OH-].[Na+]>C(=O)=O.C(O)C.C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[S:29][C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[CH:9][C:8]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 20386701HCID 20386701, compound

Product 1

HCID 203866642,3-Diphenyl-5-m-anisylthiopheneYield 82.3%

Reagents, catalysts & solvents 3

HCID 280Carbon DioxideSolventHCID 702EthanolSolventHCID 7237O-XyleneSolvent

Procedure

In a 1-liter stainless steel autoclave equipped with stirrer were placed 51.6 g (0.150 mole) of 1,2-diphenyl-4-m-anisylbutane-1,4-dione, 100 ml of xylene and 30 g (0.0675 mole) of phosphorus pentasulfide. The autoclave was cooled in Dry Ice and charged with 130 g (3.81 moles) of hydrogen sulfide. The mixture was then heated and stirred 235 minutes at 154°-177° C. (1120-1320 psig). The vessel was cooled to room temperature. The hydrogen sulfide was vented into a sodium hydroxide solution. The residue was treated with 150 ml of absolute ethanol to destroy excess phosphorus sulfides. Washing the product with another 330 ml of ethanol gave 32 g (62.3%) of crude product. Recrystallization from 50 ml of toluene and 150 ml of ethanol gave 19.8 g (38.5%) of pure 2,3-diphenyl-5-m-anisylthiophene, m.p. 100°-102° C.

Workup

  1. temperatureThe mixture was then heated
  2. customto destroy excess phosphorus sulfides
  3. washWashing the product with another 330 ml of ethanol
  4. customgave 32 g (62.3%) of crude product
  5. customRecrystallization from 50 ml of toluene and 150 ml of ethanol

Sources & evidence

ORD record
ord-c97a814917c94e0094771d1c78b58c6e
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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