Hydrochloric Acid → N-ethyl-3-(3-ethoxy-4-nitrophenyloxy)-5-methylpyrazole-1-carboxamide

HRID 644861Notes

Reaction equation

HRID 644861 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([O:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[CH3:14].Cl>C(OCC)(=O)C>[CH2:8]([NH:10][C:11]([N:28]1[C:29]([CH3:31])=[CH:30][C:26]([O:25][C:18]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([O:15][CH2:13][CH3:14])[CH:17]=2)=[N:27]1)=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178624163-(3-Ethoxy-4-nitrophenyloxy)-5-methylpyrazole

Product 1

HCID 17862462N-ethyl-3-(3-ethoxy-4-nitrophenyloxy)-5-methylpyrazole-1-carboxamideYield 64.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.07 g, 0.7 mmol) and ethyl isocyanate (0.12 g, 0.7 mmol) were added to a solution of 3-(3-ethoxy-4-nitrophenyloxy)-5-methylpyrazole (0.16 g, 0.6 mmol) in ethyl acetate (5 ml) at 0° C., and the mixture was allowed to have room temperature gradually and stirred for 5 hours. 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=1/15), to give a yellow solid of N-ethyl-3-(3-ethoxy-4-nitrophenyloxy)-5-methylpyrazole-1-carboxamide (0.13 g, yield: 61.8%). mp: 110-112° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.24 (t, J=7.3 Hz, 3H), 1.49 (t, J=7.0 Hz, 3H), 2.63 (d, J=0.5 Hz, 3H), 3.40 (dq, J=6.0 and 7.3 Hz, 2H), 4.14 (q, J=7.0 Hz, 2H), 5.80 (q, J=0.5 Hz, 1H), 6.73 (dd, J=2.4 and 9.0 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 6.92 (br s, 1H), 7.92 (d, J=9.0 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=1/15)

Sources & evidence

ORD record
ord-9538a00f6bcd4606b87a0cac22fc9fb4
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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