Hydrogen Sulfide → 2,3-Diphenyl-5-(3,4,5-trimethoxyphenyl)thiophene

HRID 46665Notes

Reaction equation

[C:1]1([C:7](=O)[CH:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9][C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[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:40].S>C(O)C>[C:1]1([C:7]2[S:40][C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)=[CH:9][C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 10 °C

Procedure

In a 1-liter stirred stainless steel autoclave were placed 40.4 g 1,2-diphenyl-4-(3,4,5-trimethoxyphenyl)butane-1,4-dione, 100 ml of xylene, 22.2 g of phosphorus pentasulfide and 128 g of hydrogen sulfide. The reaction mixture was heated with stirring for 3 hours at 160°-168° C. (1210-1250 psig. pressure). The reactor was cooled to 10° C. and the hydrogen sulfide was released. The residue was stirred with 150 ml of ethanol to decompose unreacted phosphorus pentasulfide. Filtration and evaporation gave 38.8 g (96.4%) of 2,3-diphenyl-5-(3,4,5-trimethoxyphenyl)thiophene.

Workup

temperatureThe reaction mixture was heated
filtrationFiltration and evaporation

Sources & evidence

ORD record: ord-5c2943a3f5774ae3b4901fa4fcdbce15
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04174405

Reaction notes

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