Water → HCID 15859747, compound

HRID 1635699Notes

Reaction equation

HRID 1635699 reaction equation
C(=O)([O-])[O-].[Ca+2].[C:6]1([S:12](Cl)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([CH3:29])[C:23]=1[S:24][CH2:25][N+:26]([O-:28])=[O:27])[NH2:20].O>O1CCCC1>[CH3:29][C:22]1[CH:21]=[C:19]([NH:20][S:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:14])=[O:13])[CH:18]=[C:17]([CH3:16])[C:23]=1[S:24][CH2:25][N+:26]([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 10112Calcium CarbonateHCID 18676551HCID 18676551, compound

Product 1

HCID 15859747HCID 15859747, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.75 g (7.49 mmol) of calcium carbonate and then 1.0 g (5.66 mmol) of benzenesulphonyl chloride are added to a solution, maintained under a nitrogen atmosphere, of 0.80 g (3.77 mmol) of 3,5-dimethyl-4-[(nitromethyl)thio]aniline in 30 ml of anhydrous tetrahydrofuran. After stirring for 3 days at room temperature, the reaction medium is poured into water and extracted with methylene chloride. The combined organic extracts are washed with 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 0.9 g (68%) of N-[3,5-dimethyl-4-[(nitromethyl)thio]phenyl]benzenesulphonamide.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with water
  3. dry with materialdried over sodium Sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica (eluent: methylene chloride)

Sources & evidence

ORD record
ord-d4f6bb92b3d64340b8147fd5a85019db
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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