1,2-Diphenylethanethione → 2-Phenyl-1-benzothiophene

HRID 1937646Notes

Reaction equation

HRID 1937646 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O>[C:10]1([C:8]2[S:9][C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=3[CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 5781961,2-Diphenylethanethione

Product 1

HCID 6108862-Phenyl-1-benzothiopheneYield 55.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

2-Phenylthioacetophenone (63.8 g) was added to 450 g of polyphosphoric acid at 100° C. and then heated further to 190° C. for three hours. The reaction was allowed to cool below 100° C. before pouring it into a mixture of ice and water. The aqueous solution was extracted with ether. The ether layer was dried with magnesium sulfate and evaporated to yield a tan, amorphous solid. The residue was crystallized from acetone-ethanol to give 35.2 g of the title compound. mp 171° C.-172° C.

Workup

  1. temperatureto cool below 100° C.
  2. additionbefore pouring it
  3. extractionThe aqueous solution was extracted with ether
  4. dry with materialThe ether layer was dried with magnesium sulfate
  5. customevaporated
  6. customto yield a tan, amorphous solid
  7. customThe residue was crystallized from acetone-ethanol

Sources & evidence

ORD record
ord-34b97a113c2246f6a9759704c19bfa5d
Source dataset
uspto-grants-2002_05
Patent number
US06395769B1

Reaction notes

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