Hydrochloric Acid → HCID 18676517, compound

HRID 1635703Notes

Reaction equation

HRID 1635703 reaction equation
N1C=CC=CC=1.[OH-].[K+].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[S:17](Cl)(=[O:19])=[O:18].[CH3:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([CH3:36])[C:28]=1[S:29]([CH2:32][N+:33]([O-:35])=[O:34])(=[O:31])=[O:30])[NH2:25].Cl>O1CCCC1.O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[S:17]([NH:25][C:24]1[CH:23]=[C:22]([CH3:21])[C:28]([S:29]([CH2:32][N+:33]([O-:35])=[O:34])(=[O:31])=[O:30])=[C:27]([CH3:36])[CH:26]=1)(=[O:19])=[O:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14797Potassium HydroxideHCID 195716Ici 222155HCID 27342732,4-Difluorobenzenesulfonyl Chloride

Product 1

HCID 18676517HCID 18676517, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

0.65 g (8.22 mmol) of pyridine, dried over potassium hydroxide, and 1.3 g (6.11 mmol) of 2,4-difluorobenzenesulphonyl chloride are successively added to a solution, cooled to about 10° C., of 1.0 g (4.09 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 20 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 2 h at 10° C. and then for 20 h at room temperature, after which it is poured into 100 ml of water. The mixture is brought to pH 3 by addition of concentrated hydrochloric acid and then extracted with methylene chloride. The combined organic extracts are washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The oily residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) and by recrystallization from toluene, to give 0.38 g (22%) of 2,4-difluoro-N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]benzenesulphonamide.

Workup

  1. additionare successively added to a solution
  2. waitfor 20 h at room temperature
  3. extractionextracted with methylene chloride
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe oily residue obtained
  8. customis purified by chromatography on a column of silica (eluent: methylene chloride) and by recrystallization from toluene

Sources & evidence

ORD record
ord-26e7b968e51d4373ad4b5f60c6d997f0
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

Loading…