Dichloromethane → HCID 14576905, compound

HRID 1904624Notes

Reaction equation

HRID 1904624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:22])=[CH:4][CH:3]=1.C(Cl)Cl.S(Cl)(Cl)(=O)=[O:27].C(=O)([O-])O.[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:15]=[CH:16][C:17]([S:20]([CH3:21])=[O:27])=[CH:18][CH:19]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 14576866HCID 14576866, compound

Product 1

HCID 14576905HCID 14576905, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 7.7 g of 1-(4-chlorophenyl)-6-(4-methylthiophenyl)-2-piperidone, 80 ml of methylene chloride, 3 g of silica gel, and 2.2 g of water was added 3.44 g of sulfuryl chloride at 15° to 25° C., and the mixture was stirred at 15° to 25° C. for 2 hours. The reaction mixture was poured into a cold aqueous sodium hydrogen carbonate solution. The methylene chloride solution was washed with a saturated aqueous sodium chloride solution, dried, and concentrated. The residue was purified by silica gel column chromatography (solvent; ethyl acetate:ethanol=10:1) and recrystallization from ethyl acetate to give 7.69 g of 1-(4-chlorophenyl)-6-(4-methylsulfinylphenyl)-2-piperidone as colorless prisms.

Workup

  1. washThe methylene chloride solution was washed with a saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (solvent; ethyl acetate:ethanol=10:1) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1fd930e5bbe74d2386236d9e86aeb794
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

Loading…