Hydroxyamine hydrochloride → HCID 178423542, compound

HRID 471374Notes

Reaction equation

HRID 471374 reaction equation
Cl.[NH2:2][OH:3].CC([O-])(C)C.[K+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([C:32]([F:35])([F:34])[F:33])[O:22][N:21]=[C:20]([C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([CH3:31])[CH:24]=3)[CH2:19]2)[CH:14]=[C:15]([Cl:17])[CH:16]=1>CS(C)=O>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([C:32]([F:33])([F:35])[F:34])[O:22][N:21]=[C:20]([C:23]3[CH:30]=[CH:29][C:26]([C:27]([NH:2][OH:3])=[NH:28])=[C:25]([CH3:31])[CH:24]=3)[CH2:19]2)[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 582001084-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methylbenzonitrile

Product 1

HCID 178423542HCID 178423542, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution hydroxylamine hydrochloride (8.70 g) in DMSO was cooled to 15° C., before KOtBu was added in small portions. This mixture was added to a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzonitrile (5.00 g) in DMSO (20 mL) at room temperature and stirred at 80° C. for 5 h. After completion of the reaction, the mixture was poured onto ice-water and the resulting solid was collected by filtration, washed with water and dried. Chromatography on silica gel yielded the title compound (3.3 g, 61%).

Workup

  1. additionwas added in small portions
  2. customAfter completion of the reaction
  3. additionthe mixture was poured onto ice-water
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b9d39586c04b48fbbfb4c38af4a3b9ab
Source dataset
uspto-grants-2014_01
Patent number
US08633134B2

Reaction notes

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