Hydrochloric Acid → HCID 17862350, compound

HRID 644839Notes

Reaction equation

HRID 644839 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.[N+:10]([C:13]1[C:14](F)=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)([O-:12])=[O:11].Cl>CN(C=O)C>[N+:19]([C:17]1[CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[C:15]([C:22]([F:23])([F:24])[F:25])[C:16]=1[O:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-HCID 17862438HCID 17862438, compound

Product 1

HCID 17862350HCID 17862350, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (60% in oil, 0.2 g, 5.5 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (0.49 g, 5.0 mmol) and 3,5-dinitro-2-fluorobenzotrifluoride (1.35 g, 5.0 mmol) in DMF (10 ml), and the mixture was stirred under heating at 70° C. for 6 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (30 ml) 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=1/7), to give a yellowish solid of 3-(2,4-dinitro-6-trifluoromethylphenyloxy)-5-methylpyrazole (0.58 g, yield: 34.9%). mp: 145-147° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.29 (s, 3H), 5.84 (s, 1H), 8.82 (m, 2H), 9.01 (d, J=2.7 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=1/7)

Sources & evidence

ORD record
ord-289e0347da5f4c358ffad98f8d132ef8
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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