Water → HCID 18676556, compound

HRID 1635709Notes

Reaction equation

HRID 1635709 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([CH3:30])[C:22]=1[S:23]([CH2:26][N+:27]([O-:29])=[O:28])(=[O:25])=[O:24])[NH2:19].C(=O)([O-])[O-].[Ca+2].O>O1CCCC1>[CH3:30][C:21]1[CH:20]=[C:18]([NH:19][S:9]([C:8]2[CH:13]=[CH:14][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:11])=[O:10])[CH:17]=[C:16]([CH3:15])[C:22]=1[S:23]([CH2:26][N+:27]([O-:29])=[O:28])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8481N-Acetylsulfanilyl chlorideHCID 10112Calcium CarbonateHCID 195716Ici 222155

Product 1

HCID 18676556HCID 18676556, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.9 g (12.4 mmol) of N-acetylsulphanilyl chloride are added portionwise to a mixture, maintained under a nitrogen atmosphere, of 2.0 g (8.19 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline and 1.6 g (16.0 mmol) of calcium carbonate in 40 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 6 h at room temperature and is then refluxed for 2 h, after which it is poured into 200 ml of water. The mixture is extracted 3 times 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 crystallized by trituration from a mixture of hexane and ethyl acetate. These crystals are washed with a mixture of methylene chloride and methanol at room temperature and then with a mixture of hexane and ethyl acetate at reflux, and finally with ethanol at room temperature, to give 0.26 g (7.2%) of N-[4-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenylsulphamoyl]phenyl]acetamide.

Workup

  1. temperatureis then refluxed for 2 h
  2. extractionThe mixture is extracted 3 times with methylene chloride
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe oily residue obtained
  7. customis crystallized by trituration from a mixture of hexane and ethyl acetate
  8. washThese crystals are washed with a mixture of methylene chloride and methanol at room temperature
  9. additionwith a mixture of hexane and ethyl acetate
  10. temperatureat reflux

Sources & evidence

ORD record
ord-8d9e34177ef6495f952a219818044a5e
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

Loading…