Hydrochloric Acid → N-(2-chloroethyl)-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 644883Notes

Reaction equation

HRID 644883 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13].[Cl:14][C:15]1[C:16]([O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])=[N:17][NH:18][C:19]=1[CH3:20].Cl>C(OCC)(=O)C>[Cl:8][CH2:9][CH2:10][NH:11][C:12]([N:18]1[C:19]([CH3:20])=[C:15]([Cl:14])[C:16]([O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])=[N:17]1)=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 178624724-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

Product 1

HCID 17862426N-(2-chloroethyl)-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.10 g, 1.0 mmol) and 2-chloroethyl isocyanate (0.12 g, 1.1 mmol) were added to a solution of 4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.35 g, 1.0 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 8 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 (ethyl acetate/hexane=1/10), to give a white solid of N-(2-chloroethyl)-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.44 g, yield: 97.6%). mp: 141-143° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.62 (s, 3H), 3.55-3.65 (m, 4H), 6.80-7.05 (m, 1H), 7.67 (s, 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 (ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-6b0b932e1ac54784a11bf99db06cf53a
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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