Chloroform → (4aS,8aS)-3,3-Dichlorooctahydroquinolin-2(1H)-one

HRID 2107120Notes

Reaction equation

HRID 2107120 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[NH:7]1[C@@H:16]2[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10]C[C:8]1=[O:17].S(Cl)(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH:29]([Cl:32])(Cl)[Cl:30]>>[Cl:30][C:29]1([Cl:32])[CH2:10][C@H:11]2[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12]2)[NH:7][C:8]1=[O:17]

Participants

6

Reactant 5

HCID 6212Chloroform2×HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 24819Phosphorus pentachlorideHCID 67592240HCID 67592240, compound

Product 1

HCID 71412511(4aS,8aS)-3,3-Dichlorooctahydroquinolin-2(1H)-one

Conditions

Temperature
0 °C

Procedure

28.8 g of phosphorus pentachloride were added to a solution of 23 g of cis-octahydro-1H-quinolin-2-one in 350 ml of anhydrous chloroform. To this were added dropwise 43.1 g of sulfuryl chloride in 45 ml of anhydrous chloroform at 20° to 30° C. within 30 min and the reaction mixture was stirred at the boiling point for 5 hours. After allowing to stand overnight, the mixture was neutralized with aqueous potassium carbonate cooled to 0° C. The aqueous phase was extracted twice with methylene chloride. The combined organic phases were dried over sodium sulfate and concentrated. The residue was recrystallized from ethanol with the addition of active charcoal. 32 g of pale yellow crystals, having a melting point of 176° to 177° C., were obtained.

Workup

  1. waitto stand overnight
  2. extractionThe aqueous phase was extracted twice with methylene chloride
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethanol with the addition of active charcoal
  6. customwere obtained

Sources & evidence

ORD record
ord-4096f5794286411ab4c834019d02a093
Source dataset
uspto-grants-1990_06
Patent number
US04933361

Reaction notes

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