Thionyl Chloride → 3-chloromethyl-2-N-methylthiophenesulfonamide

HRID 1448783Notes

Reaction equation

HRID 1448783 reaction equation
O[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[S:8]([NH:11][CH3:12])(=[O:10])=[O:9].S(Cl)([Cl:15])=O>>[Cl:15][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[S:8]([NH:11][CH3:12])(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 70594324HCID 70594324, compound

Product 1

HCID 166399073-chloromethyl-2-N-methylthiophenesulfonamide

Procedure

7.5 g (36.1 mmol) of 3-hydroxymethyl-2-N-methylthiophenesulfonamide are boiled under reflux with 50 ml of thionyl chloride for 15 minutes. Thereafter, the mixture is evaporated to dryness in a water-jet vacuum. The residue is taken up in 150 ml of methylene chloride and stirred with saturated sodium bicarbonate solution until the aqueous phase has an alkaline reaction. The phases are separated. The aqueous phase is extracted with two 50 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate and evaporated to give an oil which crystallizes out in the cold. There is obtained 3-chloromethyl-2-N-methylthiophenesulfonamide of melting point 52°-53° C.

Workup

  1. customThereafter, the mixture is evaporated to dryness in a water-jet vacuum
  2. customan alkaline reaction
  3. customThe phases are separated
  4. extractionThe aqueous phase is extracted with two 50 ml portions of methylene chloride
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated
  7. customto give an oil which
  8. customcrystallizes out in the cold

Sources & evidence

ORD record
ord-b0743dbf01cf4aef9ce2e54aea1f7bd2
Source dataset
uspto-grants-1980_02
Patent number
US04187303

Reaction notes

Loading…