Sulfuryl chloride → HCID 17862440, compound

HRID 644915Notes

Reaction equation

HRID 644915 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH:6]([NH:9][C:10]([N:12]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=2[Cl:30])=[N:13]1)=[O:11])([CH3:8])[CH3:7]>C(O)(=O)C>[CH:6]([NH:9][C:10]([N:12]1[C:16]([CH3:17])=[C:15]([Cl:4])[C:14]([O:18][C:19]2[C:20]([Cl:30])=[CH:21][C:22]([C:26]([F:29])([F:27])[F:28])=[CH:23][C:24]=2[Cl:25])=[N:13]1)=[O:11])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 17862328HCID 17862328, compound

Product 1

HCID 17862440HCID 17862440, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (0.16 g, 1.2 mmol) was added to a solution of N-isopropyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.40 g, 1.0 mmol) in acetic acid (5 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into ice water 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. 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=1/20), to give a white solid of N-isopropyl-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.19 g, yield: 44.1%) [mp: 109-111° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.20 (d, J=7.5 Hz, 6H), 2.61 (s, 3H), 3.85-4.10 (m, 1H), 6.25-6.50 (m, 1H), 7.67 (s, 2H).] and a white solid of N-isopropyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-trichloromethylpyrazole-1-carboxamide (0.04 g, yield: 8.0%) [mp: 105-106° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.22 (d, J=6.5 Hz, 6H), 3.85-4.15 (m, 1H), 6.25-6.55 (m, 1H), 7.69 (s, 2H), 8.24 (s, 1H)].

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
  7. distillationThe solvent was distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/20)

Sources & evidence

ORD record
ord-99316f5c6ab14a9b8e45a94e562cea4d
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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