Hydrogen Sulfide → HCID 20386623, compound

HRID 46666Notes

Reaction equation

[C:1]1([C:7](=O)[CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30].S.[OH-].[Na+]>C(O)C.C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[S:30][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])=[CH:9][C:8]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a 1-l stainless steel autoclave were placed 56.2 g (0.150 mole) of 1,2-diphenyl-4-(2,4-dimethoxyphenyl)butane-1,4-dione, 100 ml of xylene, 33.3 g (0.075 mole) of phosphorus pentasulfide and 120 g of hydrogen sulfide. The contents of the autoclave were stirred at 160°-162° C. (1040-1080 psig) for three hours. The autoclave was then cooled, and the remaining hydrogen sulfide was vented into a trap of aqueous sodium hydroxide. The residue was stirred with 150 ml of absolute ethanol to destroy excess phosphorus pentasulfide. Chilling to -78° C. and filtration gave 27.6 g (49.4%) of crude product, m.p. 107°-110° C. Recrystallization from 30 ml of dioxane and 60 mll of ethanol gave 17.3 g (31%) of pure 2,3-diphenyl-5-(2,4-dimethoxyphenyl)thiophene, m.p. 112°-114° C.

Workup

temperatureThe autoclave was then cooled
customto destroy excess phosphorus pentasulfide
filtrationfiltration
customgave 27.6 g (49.4%) of crude product, m.p. 107°-110° C
customRecrystallization from 30 ml of dioxane and 60 mll of ethanol

Sources & evidence

ORD record: ord-dab0657f93fa4b42ba3a1fe5153c2d75
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04174405

Reaction notes

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