Hydrochloric Acid → HCID 18676552, compound

HRID 1635706Notes

Reaction equation

HRID 1635706 reaction equation
N1C=CC=CC=1.[OH-].[K+].[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([CH3:38])[C:30]=1[S:31]([CH2:34][N+:35]([O-:37])=[O:36])(=[O:33])=[O:32])[NH2:27].Cl>O1CCCC1.O>[CH3:38][C:29]1[CH:28]=[C:26]([NH:27][S:19]([C:16]2[CH:17]=[CH:18][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:25]=[C:24]([CH3:23])[C:30]=1[S:31]([CH2:34][N+:35]([O-:37])=[O:36])(=[O:33])=[O:32]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14797Potassium HydroxideHCID 195716Ici 222155HCID 27351824-Methanesulfonylbenzene-1-sulfonyl chloride

Product 1

HCID 18676552HCID 18676552, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.31 ml (16.2 mmol) of pyridine, dried over potassium hydroxide, and 2.5 g (9.82 mmol) of 4-(methylsulphonyl)benzenesulphonyl chloride are successively added to a solution, maintained under a nitrogen atmosphere, of 1.6 g (6.55 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 50 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 2 days at room temperature and then poured into 200 ml of water. The mixture obtained is brought to pH 3 by addition of 1N hydrochloric acid and is then extracted with 3 times 200 ml of ethyl acetate. The combined organic extracts are washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a column of silica (eluent: 2/1 methylene chloride/ethyl acetate) and recrystallization from a mixture of hexane and ethyl acetate, to give 0.78 g (26%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-4-(methylsulphonyl)benzenesulphonamide.

Workup

  1. additionare successively added to a solution
  2. customThe mixture obtained
  3. extractionis then extracted with 3 times 200 ml of ethyl acetate
  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 residue is purified by chromatography on a column of silica (eluent: 2/1 methylene chloride/ethyl acetate) and recrystallization from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e8db4d540a644db3854bf24367a3ad86
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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