Thionyl Chloride → HCID 13290204, compound

HRID 370966Notes

Reaction equation

HRID 370966 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[S:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:8][C:7]1[C:6]([O:9][CH3:10])=[CH:5][C:4]2[C:13](=[O:15])[CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:11][C:3]=2[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 13290209HCID 13290209, compound

Product 1

HCID 13290204HCID 13290204, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A solution of 1.17 g of α-(2,3-dichloro-4-methoxyphenylthio)-α-phenylacetic acid in 25 ml of carbon disulfide is refluxed with 0.5 g of thionyl chloride until the solution becomes clear. The solution is cooled to 5° and to it is added, in small portions, 340 mg of aluminum chloride. The mixture is stirred at reflux for 3 additional hours. Ice-water (20 g) is added to quench the reaction mixture and the product is extracted into dichloromethane. The dichloromethane extract is washed with sodium bicarbonate solution, water, dried and concentrated to give a syrup. The oily residue is triturated with 2 ml of acetone and allowed to stand at room temperature. Crystals slowly deposit and are collected after 2 days. Recrystallization from chloroform gives 6,7-dichloro-5-methoxy-2-phenylbenzo[b]thiophen-3(2H)-one as a yellowish solid, mp 228°-229° C.

Workup

  1. temperatureThe solution is cooled to 5° and to it
  2. temperatureat reflux for 3 additional hours
  3. customto quench the reaction mixture
  4. extractionthe product is extracted into dichloromethane
  5. extractionThe dichloromethane extract
  6. washis washed with sodium bicarbonate solution, water
  7. customdried
  8. concentrationconcentrated
  9. customto give a syrup
  10. customThe oily residue is triturated with 2 ml of acetone
  11. customto stand at room temperature
  12. customCrystals slowly deposit and are collected after 2 days
  13. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-1976c60b92074bb6ba5ceed392d9bb37
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

Loading…