Hydroxylamine HCl → HCID 66864846, compound

HRID 1929279Notes

Reaction equation

HRID 1929279 reaction equation
[CH:1]1([C:4](=[O:28])[C:5](=[CH:24][N:25](C)C)[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[C:10]([NH:18][CH3:19])[C:9]=2[S:20]([CH3:23])(=[O:22])=[O:21])=[O:7])[CH2:3][CH2:2]1.[Cl-].O[NH3+].C([O-])(=O)C.[Na+]>C(O)C>[CH:1]1([C:4]2[O:28][N:25]=[CH:24][C:5]=2[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[C:10]([NH:18][CH3:19])[C:9]=2[S:20]([CH3:23])(=[O:22])=[O:21])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 21645Hydroxylamine HCl3×HCID 517045Sodium AcetateHCID 66864813HCID 66864813, compound

Product 1

HCID 66864846HCID 66864846, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.29 g (3.1 mmol) of 1-cyclopropyl-2-(dimethylaminomethylidene)-3-(3-methylamino-2-methylsulfonyl-4-trifluoromethylphenyl)propane-1,3-dione were introduced into 50 ml of ethanol. 0.30 g (4.3 mmol) of hydroxylammonium chloride was added, and the mixture was stirred for 30 min at RT. Thereafter, 0.33 g (4.0 mmol) of sodium acetate was added, and the contents were stirred for 16 h at RT. Thereupon, a further 0.15 g (2.2 mmol) of hydroxylammonium chloride was added, and, again, the mixture was stirred for 16 h at RT. Thereafter, a further 0.15 g (2.2 mmol) of hydroxylammonium chloride was added, and the mixture was stirred for a further 3 d at RT. The solvent was removed in vacuo, and the residue was taken up in ethyl acetate. The solution was washed with 1 N HCl, the organic phase was dried, and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel. This gave 1.00 g of product in 95% purity.

Workup

  1. stirringthe contents were stirred for 16 h at RT
  2. stirringagain, the mixture was stirred for 16 h at RT
  3. stirringthe mixture was stirred for a further 3 d at RT
  4. customThe solvent was removed in vacuo
  5. washThe solution was washed with 1 N HCl
  6. customthe organic phase was dried
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-19c27ad9a8c04e1d9217398a77325715
Source dataset
uspto-grants-2012_05
Patent number
US08188009B2

Reaction notes

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