Hydrochloric Acid → N-ethyl-5-methyl-3-(4-nitrophenyloxy)pyrazole-1-carboxamide

HRID 644850Notes

Reaction equation

HRID 644850 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:9]=[C:10]=[O:11])[CH3:8].[CH3:12][C:13]1[NH:17][N:16]=[C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[CH:14]=1.Cl>C(OCC)(=O)C>[CH2:7]([NH:9][C:10]([N:17]1[C:13]([CH3:12])=[CH:14][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[N:16]1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 178623405-Methyl-3-(4-nitrophenyloxy)pyrazole

Product 1

HCID 17862425N-ethyl-5-methyl-3-(4-nitrophenyloxy)pyrazole-1-carboxamideYield 100.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.19 g, 1.5 mmol) and ethyl isocyanate (0.09 g, 1.3 mmol) were added to a solution of 5-methyl-3-(4-nitrophenyloxy)pyrazole (0.29 g, 1.3 mmol) in ethyl acetate (15 ml), and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with diethyl ether (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=1/20), to give a white solid of N-ethyl-5-methyl-3-(4-nitrophenyloxy)pyrazole-1-carboxamide (0.38 g, yield: 99.2%). mp: 105-107° C., 1H-NMR (CDCl3, TMS, ppm): δ 1.24 (t, J=7.3 Hz, 3H), 2.64 (d, J=0.7 Hz, 3H), 3.40 (dq, J=5.9 and 7.2 Hz, 2H), 5.83 (q, J=0.7 Hz, 1H), 6.75 (m, 1H), 7.20-7.30 (m, 2H), 8.26 (dd, J=2.2 and 7.0 Hz, 2H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with diethyl ether (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=1/20)

Sources & evidence

ORD record
ord-90002f896d0d4e73a41a613d0db9da24
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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