Chloroform → HCID 21338850, compound

HRID 1879638Notes

Reaction equation

HRID 1879638 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH3:14][NH:15][CH2:16][CH3:17].C(Cl)(Cl)Cl.C(N(CC)CC)C>O>[CH2:16]([N:15]([CH3:14])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH3:17]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 12219N-MethylethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 21338850HCID 21338850, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-nitrobenzenesulfonyl chloride (5.09 g), N-methylethylamine (1.35 g) and chloroform (100 mL), triethylamine (4.11 mL) was added under ice cooling and stirred at room temperature for 5 hours. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed sequentially with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give N-ethyl-N-methyl-2-nitrobenzenesulfonamide (6.48 g) as a brown oil.

Workup

  1. additionwas added under ice cooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed sequentially with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-18856c88e6114472b0cdf80c08e112d5
Source dataset
uspto-grants-2012_11
Patent number
US08318702B2

Reaction notes

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