Ammonia → HCID 68519308, compound

HRID 386737Notes

Reaction equation

HRID 386737 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[N+:26]([O-:28])=[O:27].[NH3:29]>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.O>[Cl:24][C:22]1[CH:23]=[C:18]([C:12]2([C:14]([F:16])([F:15])[F:17])[O:11][N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][NH2:29])=[C:4]([N+:26]([O-:28])=[O:27])[CH:5]=3)[CH2:13]2)[CH:19]=[C:20]([Cl:25])[CH:21]=1

Participants

7

Reactant 2

HCID 222AmmoniaHCID 86643374HCID 86643374, compound

Product 1

HCID 68519308HCID 68519308, compound

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[4-(bromomethyl)-3-nitrophenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.0 g) in tetrahydrofuran (10 mL) was added dropwise to a solution of 28% ammonia (aqueous solution, 5 mL) and tetrabutyl ammonium iodide (0.05 g) in tetrahydrofuran (10 mL) and methanol (20 mL) under ice cooling, and the mixture was then stirred for 10 hours at room temperature. The reaction solution was diluted with water, and then extracted with ethyl acetate, and 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 yield 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-nitrophenyl}methanamine (0.8 g).

Workup

  1. extractionextracted with ethyl acetate
  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-caf8da4fea9a485f8857f89c87667e95
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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