Hydrogen Sulfide → HCID 54304945, compound

HRID 46664Notes

Reaction equation

HRID 46664 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]([C:18]([CH3:21])([CH3:20])[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:38].S>C(O)C>[C:1]1([C:7]2[S:38][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)=[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

6

Reactant 4

HCID 402Hydrogen SulfideHCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 20386660HCID 20386660, compound

Product 1

HCID 54304945HCID 54304945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1-liter stirred autoclave was charged with 55.6 g (0.150 mole) of 1,2-diphenyl-4-p-t-butylphenylbutane-1,4-dione, 100 ml of xylene, 33.3 g (0.075 mole) of phosphorus pentasulfide and 130 g of hydrogen sulfide. The reactor was cooled and vented. The residue was stirred with 150 ml of absolute ethanol. Filtration gave a first crop of 18 g (32.6%) m.p. 108°-112° C. Chilling the filtrate and refiltering gave a second crop of 24 g (43.4%) m.p. 102°-105° C. The two crops were combined for recrystallization from a mixture of 50 ml of dioxane and 100 ml of absolute ehtanol. The pure product (31.3 g, 56.6%) had a m.p. of 117°-119° C.

Workup

  1. temperatureThe reactor was cooled
  2. filtrationFiltration
  3. customgave a first crop of 18 g (32.6%) m.p. 108°-112° C
  4. temperatureChilling the filtrate and refiltering
  5. customgave a second crop of 24 g (43.4%) m.p. 102°-105° C
  6. customThe two crops were combined for recrystallization from a mixture of 50 ml of dioxane and 100 ml of absolute ehtanol

Sources & evidence

ORD record
ord-22779f3b97a0432da3fbe1518ae5b786
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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