Acetic Anhydride → HCID 68520117, compound

HRID 386738Notes

Reaction equation

HRID 386738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30].C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:26])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:29](=[O:31])[CH3:30])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68519308HCID 68519308, compound

Product 1

HCID 68520117HCID 68520117, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-nitrophenyl}methanamine (0.3 g) and acetic anhydride (0.1 g) in dichloromethane (50 mL), a solution of triethylamine (0.1 g) in dichloromethane (5 mL) was added dropwise under ice cooling, and the mixture was then stirred for one hour at room temperature. The reaction solution was diluted with water, and the organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatogaphy to yield N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-nitrobenzyl}acetamide (0.2 g).

Workup

  1. dry with materialthe organic layer was then dried over anhydrous magnesium sulfate
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was then purified by silica gel chromatogaphy

Sources & evidence

ORD record
ord-9a38f6c7c6e24fc38956ae6c2a8a21e6
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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