Sulfuryl chloride → HCID 17862337, compound

HRID 644914Notes

Reaction equation

HRID 644914 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([NH:12][C:13]([N:15]1[C:19]([CH3:20])=[CH:18][C:17]([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:16]1)=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(O)(=O)C>[CH2:6]([NH:12][C:13]([N:15]1[C:19]([CH3:20])=[C:18]([Cl:4])[C:17]([O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:30])[F:31])=[CH:24][C:23]=2[Cl:33])=[N:16]1)=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 17862417HCID 17862417, compound

Product 1

HCID 17862337HCID 17862337, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (0.16 g, 1.2 mmol) was added to a solution of N-hexyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.44 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 1/10), to give a white solid of N-hexyl-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (0.40 g, yield: 84.8%). mp: 86-88° C.; 1H-NMR (CDCl3, TMS, ppm): δ 0.88 (t, J=6.8 Hz, 3H), 1.26 (m, 6H), 1.40-1.60 (m, 2H), 2.62 (s, 3H), 3.15-3.35 (m, 2H), 6.50-6.70 (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
  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 1/10)

Sources & evidence

ORD record
ord-553cdce0db0b450eb5f9793ae4d60caf
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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