Potassium Nitrate → 2-(4-Dimethylcarbamoyl-2-methyl-phenyl)-ethanesulfonyl chloride

HRID 1754906Notes

Reaction equation

HRID 1754906 reaction equation
[N+]([O-])([O-])=O.[K+].S[CH2:7][CH2:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:20].[S:21]([Cl:25])(Cl)(=[O:23])=[O:22]>CC#N.ClCCl>[CH3:16][N:15]([CH3:17])[C:13]([C:12]1[CH:18]=[CH:19][C:9]([CH2:8][CH2:7][S:21]([Cl:25])(=[O:23])=[O:22])=[C:10]([CH3:20])[CH:11]=1)=[O:14]

Participants

6

Reactant 3

HCID 24434Potassium NitrateHCID 24648Sulfuryl chlorideHCID 866727594-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide

Product 1

HCID 866727602-(4-Dimethylcarbamoyl-2-methyl-phenyl)-ethanesulfonyl chlorideYield 74%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

Potassium nitrate (583 mg, 5.77 mmol) was added to a solution of 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide (514 mg, 2.30 mmol) in MeCN (23 ml) at room temperature. The mixture was cooled to −40° C., and sulfuryl chloride (1.68 M solution in dichloromethane, 3.46 ml, 5.81 mmol) was then added dropwise over 15 minutes. After stirring at −40° C. to −20° C. for 2.5 hours, the reaction mixture was diluted with dichloromethane (80 ml) and quenched with a saturated aqueous sodium bicarbonate solution (20 ml). The organic layer and the aqueous layer were separated, and the organic layer was then washed with a saturated aqueous sodium chloride solution (30 ml), dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2) to give 2-(4-dimethylcarbamoyl-2-methyl-phenyl)-ethanesulfonyl chloride as a colorless solid (491 mg, 74%).

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (20 ml)
  2. customThe organic layer and the aqueous layer were separated
  3. washthe organic layer was then washed with a saturated aqueous sodium chloride solution (30 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2)

Sources & evidence

ORD record
ord-3a8967aa22264254b5822a79ad3c84ac
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…