Hydrochloric Acid → HCID 17862351, compound

HRID 644853Notes

Reaction equation

HRID 644853 reaction equation
C(N(CC)CC)C.[C:8]1([N:14]=[C:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:17][C:18]1[CH:19]=[C:20]([O:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)[CH:21]=[CH:22][CH:23]=1.Cl>C(OCC)(=O)C>[C:8]1([NH:14][C:15]([N:27]2[C:28]([CH3:30])=[CH:29][C:25]([O:24][C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[CH:19]=3)=[N:26]2)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 17862402HCID 17862402, compound

Product 1

HCID 17862351HCID 17862351, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.13 g, 1.3 mmol) and phenyl isocyanate (0.15 g, 1.3 mmol) were added to a solution of 3-(3-chlorophenyloxy)-5-methylpyrazole (0.25 g, 1.2 mmol) in ethyl acetate (5 ml) at 0° C., and while the mixture was allowed to have room temperature gradually, it was stirred for 6 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 viscous substance of N-phenyl-3-(3-chlorophenyloxy)-5-methylpyrazole-1-carboxamide (0.34 g, yield: 84.5%). 1H-NMR (CDCl3, TMS, ppm): δ 2.66 (d, J=0.8 Hz, 3H), 5.78 (q, J=0.8 Hz, 1H), 7.05-7.11 (m, 1H), 7.14-7.21 (m, 3H), 7.28-7.39 (m, 3H), 7.52-7.56 (m, 2H), 8.91 (br s, 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-67d84ea37c2c4a228ce39dff4600c269
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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