Hydrochloric Acid → HCID 17862441, compound

HRID 644880Notes

Reaction equation

HRID 644880 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]=[C:9]=[O:10].[CH2:11]([C:13]1[C:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=2[C:29]([F:32])([F:31])[F:30])=[N:15][NH:16][C:17]=1[CH3:18])[CH3:12].Cl>C(OCC)(=O)C>[CH3:7][NH:8][C:9]([N:16]1[C:17]([CH3:18])=[C:13]([CH2:11][CH3:12])[C:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=2[C:29]([F:30])([F:31])[F:32])=[N:15]1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 17862454HCID 17862454, compound

Product 1

HCID 17862441HCID 17862441, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.50 g, 3.6 mmol) and methyl isocyanate (0.17 g, 3.0 mmol) were added to a solution of 4-ethyl-5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole (1.13 g, 3.6 mmol) in ethyl acetate (15 ml), and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with diethyl ether (20 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and 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=1/3), to give a yellow solid of N-methyl-4-ethyl-5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (0.71 g, yield: 63.6%). mp: 96-97° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.08 (t, J=7.6 Hz, 3H), 2.35 (q, J=7.6 Hz, 2H), 2.59 (s, 3H), 2.94 (d, J=5.0 Hz, 3H), 6.70-6.90 (m, 1H), 7.48 (d, J=9.2 Hz, 1H), 8.40 (dd, J=2.7 and 9.2 Hz, 1H), 8.60 (d, J=2.7 Hz, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with diethyl ether (20 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, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-cec1f900da764bea945b9d1b811e7fb7
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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