Hydrochloric Acid → HCID 17862381, compound

HRID 644893Notes

Reaction equation

HRID 644893 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([Cl:24])[C:15]=1[O:25][C:26]1[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[NH:28][N:27]=1.Cl>C(OCC)(=O)C>[Cl:24][C:16]1[CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=[C:14]([Cl:13])[C:15]=1[O:25][C:26]1[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[N:28]([C:11](=[O:12])[NH:10][CH2:8][CH3:9])[N:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 17862387HCID 17862387, compound

Product 1

HCID 17862381HCID 17862381, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.20 g, 2.0 mmol) and ethyl isocyanate (0.14 g, 2.0 mmol) were added to a solution of methyl 3-(2,6-dichloro-4-trifluoromethylphenyloxy)pyrazole-5-carboxylate (0.53 g, 1.5 mmol) in ethyl acetate (10 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 ethyl acetate (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 (chloroform), to give a white solid of methyl 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-1 (N-ethylcarbamoyl)pyrazole-5-carboxylate (0.15 g, yield: 23.5%). mp: 88-90° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.20 (t, J=7.3 Hz, 3H), 3.37 (dq, J=6.0 and 7.3 Hz, 2H), 3.95 (s, 3H), 6.21 (s, 1H), 6.40-6.60 (m, 1H), 7.68 (d, J=0.5 Hz, 2H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (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 (chloroform)

Sources & evidence

ORD record
ord-faf67ef6bd1e4b61b8b11f584526ae25
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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