Acetyl chloride → HCID 67190472, compound

HRID 386729Notes

Reaction equation

HRID 386729 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>O1CCCC1.C(OC)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:23])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:33](=[O:35])[CH3:34])=[CH:18][CH:19]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 44628234HCID 44628234, compound

Product 1

HCID 67190472HCID 67190472, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]phenyl}methanamine (0.2 g) and triethylamine (0.08 g) in tetrahydrofuran (5 mL), acetyl chloride (0.05 g) was added dropwise and the mixture was stirred for one hour at room temperature. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatography to obtain N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]benzyl}acetamide (0.05 g).

Workup

  1. washthe solution was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-f1571d3eb24e418980841a8d9d8c14e8
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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