Dimethylamine → 4-bromo-N,N,2-trimethylbenzenesulfonamide

HRID 912571Notes

Reaction equation

HRID 912571 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([CH3:15])[CH:6]=1>C1COCC1>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:2]([CH3:3])[CH3:1])(=[O:13])=[O:12])=[C:7]([CH3:15])[CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 27813384-Bromo-2-methylbenzenesulfonyl chloride

Product 1

HCID 595902374-bromo-N,N,2-trimethylbenzenesulfonamideYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 40% dimethylamine (aqueous, 2.5 mL, 20 mmol) in THF (2.5 mL) added 4-bromo-2-methylbenzenesulfonyl chloride (0.27 g, 1.0 mmol) with stirring. After 5h the reaction mixture was partitioned between DCM (50 mL) and water (50 mL), washed with water (2×50 mL) and brine (50 mL), dried (anhyd Na2SO4) and concentrated under reduced pressure to provide the title compound (0.28 g, quant) as a colorless liquid, which was used without purification in the next step. 1H-NMR (CDCl3) δ 7.74 (1H, d, J=8.3), 7.49 (1H, d, J=1.8), 7.46 (1H, dd, J=1.8, 8.3), 2.80 (6H, s), 2.60 (3H, s); Rf=0.38 (silica, 1:4 EtOAc/Hex).

Workup

  1. customAfter 5h the reaction mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried (anhyd Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f18a726bff040329397ff1e19ea8c46
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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