Sulfuryl chloride → HCID 17862459, compound

HRID 644913Notes

Reaction equation

HRID 644913 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][NH:7][C:8]([N:10]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[C:26]([F:29])([F:28])[F:27])=[N:11]1)=[O:9]>C(O)(=O)C>[CH3:6][NH:7][C:8]([N:10]1[C:14]([CH3:15])=[C:13]([Cl:4])[C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[C:26]([F:29])([F:28])[F:27])=[N:11]1)=[O:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 17862421HCID 17862421, compound

Product 1

HCID 17862459HCID 17862459, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (0.16 g, 1.2 mmol) was added to a solution of N-methyl-5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (0.34 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-methyl-4-chloro-5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole-1-carboxamide (0.27 g, yield: 71.2%). mp: 157-158° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.66 (s, 3H), 2.96 (d, J=5.0 Hz, 3H), 6.70-6.95 (m, 1H), 7.31 (d, J=9.2 Hz, 1H), 8.41 (dd, J=2.7 and 9.2 Hz, 1H), 8.62 (d, J=2.7 Hz, 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=1/10)

Sources & evidence

ORD record
ord-9536f13160af4ade90ce5d0fd717e2cf
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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