Triethylamine → 2-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamide

HRID 1110145Notes

Reaction equation

HRID 1110145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].Cl.[CH3:16][NH:17][CH3:18].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:16][N:17]([CH3:18])[S:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Product 1

HCID 201055802-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamideYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 80 g of 2-chloro-5nitrobenzenesulfonyl chloride (Example A-1 above) in 200 ml of methylene chloride heated to reflux, was slowly added a solution of 30 g of dimethylamine hydrochloride in 30 ml of water followed by a dropwise addition of triethylamine. After completion of the addition, the reaction mixture was refluxed for 20 minutes, cooled to room temperature and concentrated by rotatory evaporation. The residue was treated with water and the resulting solid was filtered and recrystallized from ethanol, affording 61 g of the title compound, mp 138°-140° C.

Workup

  1. temperatureto reflux
  2. additionAfter completion of the addition
  3. temperaturethe reaction mixture was refluxed for 20 minutes
  4. concentrationconcentrated by rotatory evaporation
  5. additionThe residue was treated with water
  6. filtrationthe resulting solid was filtered
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4ce918f0fb2a4331846d12e3aad9e479
Source dataset
uspto-grants-1994_06
Patent number
US05324854

Reaction notes

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