Hydrochloric Acid → HCID 18676554, compound

HRID 1635704Notes

Reaction equation

HRID 1635704 reaction equation
N1C=CC=CC=1.[OH-].[K+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[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>[CH3:36][C:27]1[CH:26]=[C:24]([NH:25][S:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH:23]=[C:22]([CH3:21])[C:28]=1[S:29]([CH2:32][N+:33]([O-:35])=[O:34])(=[O:31])=[O:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 195716Ici 222155

Product 1

HCID 18676554HCID 18676554, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.33 ml (16.4 mmol) of pyridine, dried over potassium hydroxide, and 2.54 g (12.3 mmol) of 4-methoxybenzenesulphonyl 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 40 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 24 h at room temperature and is then maintained at 40° C. for 1 h, after which it is poured into a mixture of water and ice. The aqueous solution obtained is brought to pH 1 by addition of 1N hydrochloric acid and is 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 recrystallization from a mixture of hexane and ethyl acetate, to give 1.1 g (33%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-4-methoxybenzenesulphonamide.

Workup

  1. additionare successively added to a solution
  2. temperatureis then maintained at 40° C. for 1 h
  3. customThe aqueous solution obtained
  4. extractionis extracted with methylene chloride
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe oily residue obtained
  9. customis purified by chromatography on a column of silica (eluent: methylene chloride) and recrystallization from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9d0a6959e45d4d34887e86768e8ae5f4
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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