Sulfuryl chloride → HCID 17862338, compound

HRID 644917Notes

Reaction equation

HRID 644917 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][NH:7][C:8]([N:10]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=2)=[N:11]1)=[O:9]>C(O)(=O)C>[CH3:6][NH:7][C:8]([N:10]1[C:14]([CH2:15][CH3:16])=[C:13]([Cl:4])[C:12]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:26])([F:27])[F:28])=[CH:20][N:19]=2)=[N:11]1)=[O:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 17862336HCID 17862336, compound

Product 1

HCID 17862338HCID 17862338, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (0.17 g, 1.2 mmol) was added to a solution of N-methyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-ethylpyrazole-1-carboxamide (0.35 g, 1.0 mmol) in acetic acid (5 ml), and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate (10 ml×3). The 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-methyl-4-chloro-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-ethylpyrazole-1-carboxamide (0.31 g, yield: 80.9%). mp: 88-89° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.30 (t, J=7.4 Hz, 3H), 2.96 (d, J=5.0 Hz, 3H), 3.14 (q, J=7.4 Hz, 2H), 6.90-7.10 (m, 1H), 8.04 (d, J=2.0 Hz, 1H), 8.32 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 ml×3)
  3. washThe 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-3de6b0375f0341faa84177de3100ce3b
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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