Dichloromethane → HCID 15227000, compound

HRID 864766Notes

Reaction equation

HRID 864766 reaction equation
Br[C:2]12[CH:10]3[CH2:11][CH:7]([CH:8]=[CH:9]3)[CH:6]1S[N:4]([C:12](C)(C)C)[C:3]2=[O:16].[S:17](Cl)(Cl)(=[O:19])=[O:18].[Cl:22]CCl>>[Cl:22][CH2:12][N:4]1[C:3](=[O:16])[C:2]2[CH:10]3[CH2:11][CH:7]([C:6]=2[S:17]1(=[O:19])=[O:18])[CH2:8][CH2:9]3

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 19419220HCID 19419220, compound

Product 1

HCID 15227000HCID 15227000, compoundYield 81%

Procedure

The sulfide (1.05 g, 3 mmol) in dichloromethane (100 mL) was treated with sulfuryl chloride (0.66 g, 5 mmol) and stirred for 2 hr. The resulting yellow solution was diluted with MDC (100 mL), washed with saturated NaHCO3 solution, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (33% MDC in hexanes) to give 0.66 g (81%) of 2-chloromethyl-4,5,6,7-tetrahydro-4,7-methano-1,2-benzisothiazol-3(2H)-one 1,1-dioxide.

Workup

  1. additionThe resulting yellow solution was diluted with MDC (100 mL)
  2. washwashed with saturated NaHCO3 solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (33% MDC in hexanes)

Sources & evidence

ORD record
ord-82d9bf3832684dd6809dd490aafa2f68
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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