Water → HCID 18676564, compound

HRID 1635710Notes

Reaction equation

HRID 1635710 reaction equation
C(=O)([O-])[O-].[Ca+2].[CH3:6][C:7]1[CH:8]=[C:9]([CH:11]=[C:12]([CH3:21])[C:13]=1[S:14]([CH2:17][N+:18]([O-:20])=[O:19])(=[O:16])=[O:15])[NH2:10].[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>O1CCCC1>[CH3:21][C:12]1[CH:11]=[C:9]([NH:10][S:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH:8]=[C:7]([CH3:6])[C:13]=1[S:14]([CH2:17][N+:18]([O-:20])=[O:19])(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 95884-Fluorobenzenesulfonyl chlorideHCID 10112Calcium CarbonateHCID 195716Ici 222155

Product 1

HCID 18676564HCID 18676564, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.65 g (16.5 mmol) of calcium carbonate are added to a solution of 2.0 g (8.19 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 40 ml of anhydrous tetrahydrofuran, followed by portionwise addition of 2.4 g (12.3 mmol) of 4-fluorobenzenesulphonyl chloride. The reaction medium is refluxed for 50 hours. After cooling, it is poured into 200 ml of water and 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 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 1.2 g (36%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-4-fluorobenzenesulphonamide.

Workup

  1. temperatureThe reaction medium is refluxed for 50 hours
  2. temperatureAfter cooling
  3. extractionextracted 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 oily residue obtained
  8. 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-e12a80c0268e45e1a243b21406cf7abf
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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