Water → N-(4-Chloro-3-methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamide

HRID 1744264Notes

Reaction equation

HRID 1744264 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8](=[O:19])[C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[N:11][CH:10]=2)[O:4][N:3]=1.C(Cl)(Cl)(Cl)[Cl:21].ClN1C(=O)CCC1=O.O>CCCCCC.C(OCC)(=O)C>[Cl:21][C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[NH:7][C:8](=[O:19])[C:9]1[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:12]=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 11369270N-(3-Methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamide

Product 1

HCID 12137634N-(4-Chloro-3-methyl-5-isoxazolyl)-4-(trifluoromethyl)nicotinamideYield 61%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To N-(3-methyl-5isoxazolyl)-4-(trifluoromethyl)nicotinamide (Compound No. 1-2, 101.7 mg, 0.37 mmol) prepared according to Example 1, carbon tetrachloride (2 ml) and N-chlorosuccinimide (64.6 mg, 0.48 mmol) were added, and the mixture was heated under reflux for 1.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by thin layer chromatography (a developing solvent: hexane/ethyl acetate=1/1) to obtain the title compound (69.3 mg, yield 61%).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified by thin layer chromatography (a developing solvent

Sources & evidence

ORD record
ord-65c5331ee27b46159e1d733e9cc2c66b
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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