Hydrochloric Acid → HCID 15859750, compound

HRID 1635702Notes

Reaction equation

HRID 1635702 reaction equation
N1C=CC=CC=1.[OH-].[K+].[CH3:9][C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1.[CH3:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([CH3:35])[C:27]=1[S:28]([CH2:31][N+:32]([O-:34])=[O:33])(=[O:30])=[O:29])[NH2:24].Cl>O1CCCC1.O>[CH3:35][C:26]1[CH:25]=[C:23]([NH:24][S:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH3:9])[CH:11]=2)(=[O:18])=[O:17])[CH:22]=[C:21]([CH3:20])[C:27]=1[S:28]([CH2:31][N+:32]([O-:34])=[O:33])(=[O:30])=[O:29]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14797Potassium HydroxideHCID 195716Ici 222155HCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 15859750HCID 15859750, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.3 ml (16.1 mmol) of pyridine, dried over potassium hydroxide, and 2.3 g (12.1 mmol) of 3-methylbenzenesulphonyl chloride are successively added to a solution, maintained under a nitrogen atmosphere, of 2.0 g (8.19 mmol) of 3,5-dimethyl-4-[(nitromethyl]sulphonyl]aniline in 50 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 24 h at room temperature and then maintained at 40° C. for 1 h, after which it is poured into a mixture of 100 ml of water and 100 g of ice. This mixture is acidified to pH 3 by addition of 1N hydrochloric acid and is extracted with 3 times 100 ml of methylene chloride. The combined organic extracts are washed with 100 ml of water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) to give 2.3 g (71%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-3-methylbenzenesulphonamide.

Workup

  1. additionare successively added to a solution
  2. temperaturemaintained at 40° C. for 1 h
  3. extractionis extracted with 3 times 100 ml of methylene chloride
  4. washThe combined organic extracts are washed with 100 ml of water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica (eluent: methylene chloride)

Sources & evidence

ORD record
ord-f923b693ffba413f90561b4b8955b200
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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