Hydrochloric Acid → HCID 17862395, compound

HRID 644873Notes

Reaction equation

HRID 644873 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[NH:13][N:12]=[C:11]([O:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[N:16]=2)[CH:10]=1.[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27].Cl>C(OCC)(=O)C>[CH2:26]([NH:28][C:29]([N:13]1[C:9]([CH3:8])=[CH:10][C:11]([O:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[N:16]=2)=[N:12]1)=[O:30])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 17862401HCID 17862401, compound

Product 1

HCID 17862395HCID 17862395, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.22 g, 2.2 mmol) was added to a solution of 5-methyl-3-(6-methoxy-3-nitropyridin-2-yloxy)pyrazole (0.5 g, 2.0 mmol) in ethyl acetate (10 ml), and the mixture was cooled to 0° C. Ethyl isocyanate (0.16 g, 2.2 mmol) was added, and the mixture was stirred at an ambient temperature for 30 minutes. The mixture was allowed to have room temperature. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid (10 ml) and extracted with ethyl acetate (10 ml×2). An organic layer was washed with water (10 ml×2), 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=1/6), to give a yellow viscous substance of N-ethyl-5-methyl-3-(6-methoxy-3-nitropyridin-2-yloxy)pyrazole-1-carboxamide (0.38 g, yield: 59.8%). 1H-NMR (CDCl3, TMS, ppm): δ 1.24 (t, J=7.3 Hz, 3H), 2.65 (d, J=0.8 Hz, 3H), 3.40 (dq, J=1.4 and 7.3 Hz, 2H), 3.84 (s, 3H), 6.02 (q, J=0.8 Hz, 1H), 6.57 (dd, J=3.5 and 8.8 Hz, 1H), 7.05 (br s, 1H), 8.41 (dd, J=3.5 and 8.8 Hz, 1H).

Workup

  1. customto have room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (10 ml×2)
  4. washAn organic layer was washed with water (10 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove a desiccant, and the solvent
  8. distillationwas distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/6)

Sources & evidence

ORD record
ord-ac4e94af1dc64bf8bdc65f4f33ddc5db
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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