Hydrogen Sulfide → 2,3-Di-p-anisyl-5-p-chlorophenylthiophene

HRID 46656Notes

Reaction equation

HRID 46656 reaction equation
[CH2:1]([C:10](=O)[CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:33].S.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:1]([C:10]1[S:33][C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:12][C:11]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 57264742HCID 57264742, compound

Product 1

HCID 867367012,3-Di-p-anisyl-5-p-chlorophenylthiopheneYield 153.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a 1-liter stainless steel autoclave equipped with stirrer were placed 54.5 g (0.133 mole) of 1,2-di-p-anisyl-4-p-chlorophenylbutane-1,4-dione, 100 ml of xylene and 30 g (0.0675 mole) of phosphorus pentasulfide. The autoclave was cooled with a Dry Ice-acetone bath and 130 g (3.81 moles) of hydrogen sulfide was distilled into the autoclave. The vessel was stirred and heated for three hours at 162°-168° C. (1220-1290 psig). After cooling to room temperature the hydrogen sulfide was vented into an aqueous sodium hydroxide solution. Treatment with 150 ml of absolute ethanol to remove unreacted phosphorus pentasulfide gave 77 g of crude product. Recrystallization from 400 ml of absolute ethanol gave 45 g (83.1%) of pure 2,3-di-p-anisyl-5-p-chlorophenylthiophene, m.p. 125°-128° C.

Workup

  1. temperatureThe autoclave was cooled with a Dry Ice-acetone bath
  2. temperatureheated for three hours at 162°-168° C. (1220-1290 psig)
  3. customTreatment with 150 ml of absolute ethanol to remove unreacted phosphorus pentasulfide
  4. customgave 77 g of crude product
  5. customRecrystallization from 400 ml of absolute ethanol

Sources & evidence

ORD record
ord-57d05772f0d3420799e83c85b730f450
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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