N,N'-Dimethylethylenediamine → 3-bromo-N-(2-(dimethylamino)ethyl)benzenesulfonamide

HRID 238350Notes

Reaction equation

HRID 238350 reaction equation
C[NH:2][CH2:3][CH2:4][NH:5][CH3:6].[CH2:7](N(CC)CC)C.[Br:14][C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1>C(Cl)(Cl)Cl>[Br:14][C:15]1[CH:16]=[C:17]([S:21]([NH:2][CH2:3][CH2:4][N:5]([CH3:6])[CH3:7])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 38617893-bromo-N-(2-(dimethylamino)ethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under cooling in an ice bath, N,N′-dimethylethylenediamine (414 mg) and triethylamine (1.10 mL) were added to a chloroform (10 mL) solution of 3-bromobenzenesulfonyl chloride (1.00 g), and the obtained solution was then stirred at a room temperature for 45 minutes. The reaction solution was washed with water, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel 60N, chloroform:methanol=98:2 to 96:4), so as to obtain the title compound (1.14 g) in the form of a colorless solid.

Workup

  1. temperatureUnder cooling in an ice bath
  2. washThe reaction solution was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel 60N, chloroform:methanol=98:2 to 96:4)

Sources & evidence

ORD record
ord-f01e4ddc901c4d7b840da4fc1fa1f0c5
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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