Hydrochloric Acid → HCID 17862461, compound

HRID 644870Notes

Reaction equation

HRID 644870 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[N+:12]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([C:24]([F:27])([F:26])[F:25])[C:16]=1[O:28][C:29]1[CH:33]=[C:32]([CH3:34])[NH:31][N:30]=1)([O-:14])=[O:13].Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:31]1[C:32]([CH3:34])=[CH:33][C:29]([O:28][C:16]2[C:17]([C:24]([F:26])([F:27])[F:25])=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])=[N:30]1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 17862350HCID 17862350, compound

Product 1

HCID 17862461HCID 17862461, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.15 g, 1.1 mmol) and ethyl isocyanate (0.07 g, 1.0 mmol) were added to a solution of 3-(2,4-dinitro-6-trifluoromethylphenyloxy)-5-methylpyrazole (0.33 g, 1.0 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and 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, 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=1/10), to give a yellowish solid of N-ethyl-3-(2,4-dinitro-6-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.20 g, yield: 49.6%). mp: 169-171° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.18 (t, J=7.2 Hz, 3H), 2.59 (d, J=0.4 Hz, 3H), 3.31 (dq, J=6.0 and 7.2 Hz, 2H), 5.95 (q, J=0.4 Hz, 1H), 6.25-6.50 (m, 1H), 8.85 (d, J=2.7 Hz, 1H), 9.02 (d, J=2.7 Hz, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted 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, 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=1/10)

Sources & evidence

ORD record
ord-e3e18deda73940948a131eb7201d370b
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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