Dimethylamine → HCID 53973806, compound

HRID 1288694Notes

Reaction equation

HRID 1288694 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

5

Reactant 2

HCID 674DimethylamineHCID 54557372HCID 54557372, compound

Product 1

HCID 53973806HCID 53973806, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

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

  1. waitat room temperature for a further 16 hours
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts were dried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica eluting with petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-d536df533ab6453195a3494ad8dcdb4b
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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