Hydrochloric Acid → Benzenesulfonamide, N,N,4-trimethyl-

HRID 501809Notes

Reaction equation

HRID 501809 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:13][NH:14][CH3:15].C(N(CC)CC)C.Cl>C(Cl)Cl.O>[CH3:13][N:14]([CH3:15])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 11743Benzenesulfonamide, N,N,4-trimethyl-Yield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7.00 g of 4-methylbenzenesulfonyl chloride was dissolved in 70 mL of methylene chloride, to which 3.59 g of dimethylamine hydrochloride was added at room temperature and 12.8 mL of triethylamine was added dropwise in an ice bath, and then this solution was stirred for one hour at room temperature. The reaction mixture, to which water was added, was adjusted to pH 3 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out thereof under reduced pressure to yield 6.75 g of N,N,4-trimethylbenzenesulfonamide as white solid.

Workup

  1. additionwas added at room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out thereof under reduced pressure

Sources & evidence

ORD record
ord-1a3e0f8e359f49e695c2ea51e025f648
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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