Dimethylamine → HCID 53973806, compound
Reaction equation
Br[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[CH3:24][NH:25][CH3:26]>C(O)C.ClCCl>[CH3:24][N:25]([CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1)[CH3:26]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-[bromo-(2-nitro-4-trifluoromethylphenyl)-methyl]-5-cyclopropylisoxazole (1.2 g) and dimethylamine (2.0 g of a 33% solution in ethanol) in dichloromethane was stirred at 0° C. for 2 hours and then at room temperature for a further 16 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The organic extracts were dried (anhydrous magnesium sulphate), filtered and evaporated to dryness. The residue was purified by column chromatography on silica eluting with petroleum ether and ethyl acetate to give 4-[N,N-dimethylamino-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (compound 300, 0.27 g) as a yellow oil: NMR (CDCl3); 1.02(4H, m), 2.08(1H,m), 2.12(6H,s), 4.9(1H, s), 7.8(1H, m), 7.9(1H, m), 8.0(1H,s), 8.1(1H, m).
Workup
- waitat room temperature for a further 16 hours
- customThe reaction mixture was quenched with water
- extractionextracted with dichloromethane
- dry with materialThe organic extracts were dried (anhydrous magnesium sulphate)
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified by column chromatography on silica eluting with petroleum ether and ethyl acetate
Sources & evidence
- ORD record
- ord-70d43e6c68734e6aa0be071e7e3ab1ce
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650533
Reaction notes
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