Hydrochloric Acid → HCID 17862371, compound

HRID 644856Notes

Reaction equation

HRID 644856 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([N:11]=[C:12]=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH3:14][C:15]1[NH:19][N:18]=[C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[N+:31]([O-:33])=[O:32])[CH:16]=1.Cl>CN(C=O)C>[C:7]([NH:11][C:12]([N:19]1[C:15]([CH3:14])=[CH:16][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[N+:31]([O-:33])=[O:32])=[N:18]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 62412tert-Butyl isocyanateHCID 17862373HCID 17862373, compound

Product 1

HCID 17862371HCID 17862371, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.83 g, 6.0 mmol) and tert-butyl isocyanate (0.59 g, 6.0 mmol) were added to a solution of 5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)pyrazole (1.15 g, 4.0 mmol) in DMF (10 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (20 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=1/5), to give a white solid of N-tert-butyl-5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)-pyrazole-1-carboxamide (0.80 g, yield: 51.8%). mp: 104-106° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.41 (s, 9H), 2.61 (s, 3H), 5.82 (s, 1H), 6.65-6.90 (br s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.82 (dd, J=2.1 and 8.7 Hz, 1H), 8.23 (d, J=2.1 Hz, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (20 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=1/5)

Sources & evidence

ORD record
ord-df4f767ec39040c0b464eb5e9f52ef6d
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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