Water → HCID 17862447, compound

HRID 644918Notes

Reaction equation

HRID 644918 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([NH:11][C:12]([N:14]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=2)=[N:15]1)=[O:13])[CH3:10].O>ClCCl>[CH2:9]([NH:11][C:12]([N:14]1[C:18]([CH3:19])=[C:17]([Br:1])[C:16]([O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28]([F:29])([F:30])[F:31])=[CH:23][N:22]=2)=[N:15]1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 17862339HCID 17862339, compound

Product 1

HCID 17862447HCID 17862447, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (0.64 g, 3.6 mmol) was added to a solution of N-ethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (1.05 g, 3.0 mmol) in dichloromethane (20 ml), and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant. The solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7), to give a white solid of N-ethyl-4-bromo-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.86 g, yield: 67.0%). mp: 123-125° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.23 (t, J=7.3 Hz, 3H), 2.67 (s, 3H), 3.40 (dq, J=5.9 and 7.3 Hz, 2H), 6.90-7.10 (m, 1H), 8.04 (d, J=2.0 Hz, 1H), 8.32 (m, 1H).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (10 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant
  7. distillationThe solvent was distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7)

Sources & evidence

ORD record
ord-63c28436c34d45559461b5773910900c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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