Methylamine → 4-bromo-N,3-dimethylbenzenesulfonamide

HRID 1644690Notes

Reaction equation

HRID 1644690 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][C:5]=1[CH3:14]>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:2][CH3:1])(=[O:12])=[O:11])=[CH:6][C:5]=1[CH3:14]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 84680704-bromo-N,3-dimethylbenzenesulfonamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (2.0 M in tetrahydrofuran, 46.37 mL, 92.75 mmol) was added to a stirred solution of 4-bromo-3-methyl-benzenesulfonyl chloride (5.0 g, 19 mmol) in tetrahydrofuran at 0° C., and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate (50 mL), washed with 2.0 N aqueous HCl (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 4-bromo-3-methyl-N-methyl-benzenesulfonamide (4.2 g, 85.7%) as a white solid. MS cald. for C8H10BrNO2S [M+] 264.1, obsd. 263.9.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with 2.0 N aqueous HCl (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f01455f59c94f71b7d66b60d34580e3
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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