3-Chloro-2-methyl-1-propene → Benzenesulfonamide, 4-methyl-N-(2-methyl-2-propenyl)-N-2-propenyl-

HRID 515913Notes

Reaction equation

HRID 515913 reaction equation
Cl[CH2:2][C:3]([CH3:5])=[CH2:4].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][CH:18]=[CH2:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:4][C:3]([CH3:5])=[CH2:2])[CH2:17][CH:18]=[CH2:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 297877N-Allyl-4-methylbenzenesulfonamide

Product 1

HCID 11230883Benzenesulfonamide, 4-methyl-N-(2-methyl-2-propenyl)-N-2-propenyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-2-methylpropene (20 mL, 0.20 mol) is added over a period of 5 minutes to a suspension of 4-methyl-N-(prop-2-en-1-yl)benzene-1-sulphonamide (27.9 g, 0.13 mol) and potassium carbonate (28.1 g, 0.20 mol) in N,N-dimethylformamide (200 mL) cooled in an ice bath. After 20 minutes, the suspension is stirred at ambient temperature for 18 hours. The suspension is concentrated to dryness. The residue is taken up in ethyl acetate (250 mL) and water (110 mL). The aqueous phase is extracted with ethyl acetate (2×50 mL). The combined organic phases are washed successively with aqueous 3N HCl solution (50 mL), water (3×50 mL), aqueous 5% potassium bicarbonate solution (50 mL), and finally brine (50 mL). The organic phase is dried over Na2SO4, filtered and concentrated to obtain the expected compound in the form of an oil.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe suspension is concentrated to dryness
  3. extractionThe aqueous phase is extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic phases are washed successively with aqueous 3N HCl solution (50 mL), water (3×50 mL), aqueous 5% potassium bicarbonate solution (50 mL), and finally brine (50 mL)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-efaedebd5e5d405f8af9fcc59fd1874b
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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