Hydrogen Sulfide → HCID 20386626, compound

HRID 46663Notes

Reaction equation

HRID 46663 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]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([F:20])[CH:13]=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+]>O.C(O)C.C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[S:29][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([F:20])[CH:13]=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 20386676HCID 20386676, compound

Product 1

HCID 20386626HCID 20386626, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

In a 1-liter autoclave were place 30 g (82.8 mmoles) of 1,2-diphenyl-4-(3-fluoro-4-methoxyphenyl)butane-1,4-dione, 100 ml of xylene, 18.4 g (41.4 mmoles) of phosphorus pentasulfide and 130 g of hydrogen sulfide. The vessel was heated 205 minutes at 155°-163` C. (1145-1235 psig.). The reactor was cooled and the hydrogen sulfide vented into a solution of 200 g of sodium hydroxide in 2 l of water. The semisolid residue was stirred with 150 ml of absolute ethanol. Filtration gave a first crop of 14.7 g (49.3%) m.p. 122°-125° C. Chilling the filtrate and refiltration gave a second crop of 10.5 g (35.2%), m.p. 118°-122° C. The two crops were combined and recrystallized from a mixture of 30 ml of dioxane and 70 ml of absolute ethanol to give 21.5 g (72.0%) of colorless plates, m.p. 123°-125° C.

Workup

  1. temperatureThe vessel was heated 205 minutes at 155°-163` C
  2. temperatureThe reactor was cooled
  3. filtrationFiltration
  4. customgave a first crop of 14.7 g (49.3%) m.p. 122°-125° C
  5. temperatureChilling the filtrate and refiltration
  6. customgave a second crop of 10.5 g (35.2%), m.p. 118°-122° C
  7. customrecrystallized from a mixture of 30 ml of dioxane and 70 ml of absolute ethanol
  8. customto give 21.5 g (72.0%) of colorless plates, m.p. 123°-125° C.

Sources & evidence

ORD record
ord-4a509ab6fc884d158987810cf62608f7
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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