Water → HCID 18350505, compound

HRID 430424Notes

Reaction equation

HRID 430424 reaction equation
Cl.[NH2:2]O.[Cl:4][C:5]1[CH:10]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:7][C:6]=1[C:16](=[O:27])[C:17](=[CH:23]OCC)[C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19].C([O-])(=O)C.[Na+].O>C(O)C>[Cl:4][C:5]1[CH:10]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:7][C:6]=1[C:16]([C:17]1[CH:23]=[N:2][O:19][C:18]=1[CH:20]1[CH2:22][CH2:21]1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochloride2×HCID 517045Sodium Acetate2×HCID 54052427HCID 54052427, compound

Product 1

HCID 18350505HCID 18350505, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.53 g) was added to a stirred solution of 1-[2-chloro-4-(methylsulphonylamino)phenyl]-3-cyclopropyl-2-ethoxymethylenepropane-1,3-dione (2.8 g) in ethanol. Sodium acetate (0.63 g) was then added portionwise over a period of ten minutes. The mixture was then stirred at room temperature for 0.5 hours. Further quantities of hydroxylamine hydrochloride (0.2 g) and sodium acetate (0.24 g) were added and stirring was continued for 0.5 hours. Water was added, the mixture was extracted with dichloromethane and the combined organic extracts were washed with water, dried and the solvent evaporated. The crude product was purified by column chromatography to yield 4-[2-chloro-4-(methylsulphonylamino)benzoyl]-5-cyclopropylisoxazole (compound 1) as a white solid, 1.66 g, m.p. 122.8-124.5° C.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. washthe combined organic extracts were washed with water
  5. customdried
  6. customthe solvent evaporated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-30d0f88d50a54267836bae118b77da16
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

Loading…