Hydrochloric Acid → HCID 17862345, compound

HRID 644849Notes

Reaction equation

HRID 644849 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[NH:13][N:12]=[C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=1.[CH2:21]([N:23]=[C:24]=[O:25])[CH3:22].Cl>C(OCC)(=O)C>[CH2:21]([NH:23][C:24]([N:13]1[C:9]([CH3:8])=[CH:10][C:11]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:12]1)=[O:25])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 17862370HCID 17862370, compound

Product 1

HCID 17862345HCID 17862345, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.13 g, 1.3 mmol) was added to a solution of 5-methyl-3-phenyloxypyrazole (0.20 g, 1.2 mmol) in ethyl acetate (5 ml), and the mixture cooled to 0° C. Then, ethyl isocyanate (0.09 g, 1.3 mmol) was added, and the mixture was stirred for 30 minutes at an ambient temperature. And, the mixture was stirred for 4 hours while it was allowed to have room temperature gradually. 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 viscous substance of N-ethyl-5-methyl-3-phenyloxypyrazole-1-carboxamide (0.16 g, yield: 56.4%). 1H-NMR (CDCl3, TMS, ppm): δ 1.22 (t, J=7.3 Hz, 3H), 2.58 (d, J=0.8 Hz, 3H), 3.38 (dq, J=1.3 and 7.3 Hz, 2H), 5.67 (q, J=0.8 Hz, 1H), 6.99-7.07 (br s, 1H), 7.12-7.19 (m, 3H), 7.33-7.39 (m, 2H).

Workup

  1. stirringAnd, the mixture was stirred for 4 hours while it
  2. customto have room temperature
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (10 ml×2)
  5. washAn organic layer was washed with water (10 ml×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customto remove a desiccant, and the solvent
  9. distillationwas distilled off from the filtrate under reduced pressure
  10. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/15)

Sources & evidence

ORD record
ord-6a84e2bf417b43988f15f8134b1acf1c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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