Hydroxyamine hydrochloride → HCID 12993705, compound

HRID 1006398Notes

Reaction equation

HRID 1006398 reaction equation
[CH:1]1([C:4](=[O:30])[C:5](=[CH:26]OCC)[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][N:16]3[C:20](=[O:21])[N:19]([CH:22]4[CH2:24][CH2:23]4)[N:18]=[N:17]3)[C:9]=2[Cl:25])=[O:7])[CH2:3][CH2:2]1.Cl.[NH2:32]O.C([O-])(=O)C.[Na+]>C(O)C>[CH:1]1([C:4]2[O:30][N:32]=[CH:26][C:5]=2[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][N:16]3[C:20](=[O:21])[N:19]([CH:22]4[CH2:24][CH2:23]4)[N:18]=[N:17]3)[C:9]=2[Cl:25])[CH2:2][CH2:3]1.[CH:1]1([C:4](=[O:30])[CH2:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][N:16]3[C:20](=[O:21])[N:19]([CH:22]4[CH2:24][CH2:23]4)[N:18]=[N:17]3)[C:9]=2[Cl:25])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 69743788HCID 69743788, compound

Product 2

HCID 12993705HCID 12993705, compoundHCID 12993708HCID 12993708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}-2-ethoxymethylenepropan-1,3-dione (3.22 g) and hydroxylamine hydrochloride (0.54 g) in ethanol (15 ml), sodium acetate (0.62 g) was added in several portions while stirring and the mixture was stirred at room temperature for 6 hours. The solvent was distilled off the mixture under reduced pressure and the residue was extracted with ethyl acetate (120 ml), washed with salt water and dried with anhydrous magnesium sulfate. The residue, obtained by distilling off the ethyl acetate, was purified by silica column chromatography (ethyl acetate: n-hexane=1:1) to obtain the objective 5-cyclopropyl-4-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorobenzoyl}isoxazole (2.37 g, 84% yield from 3-cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}propan-1,3-dione. nD20 : 1.5929.

Workup

  1. additionwas added in several portions
  2. stirringthe mixture was stirred at room temperature for 6 hours
  3. distillationThe solvent was distilled off the mixture under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate (120 ml)
  5. washwashed with salt water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe residue, obtained
  8. distillationby distilling off the ethyl acetate
  9. customwas purified by silica column chromatography (ethyl acetate: n-hexane=1:1)

Sources & evidence

ORD record
ord-c84db1c15ace4352a690a95a4c6a6a5e
Source dataset
uspto-grants-2004_09
Patent number
US06790810B2

Reaction notes

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