Water → HCID 24225555, compound

HRID 1686184Notes

Reaction equation

HRID 1686184 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].CC([O-])(C)C.[K+].Cl[CH2:16][C:17]1[C:18]([CH3:23])=[N:19][O:20][C:21]=1[CH3:22].O>CN(C=O)C>[CH3:23][C:18]1[C:17]([CH2:16][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)=[C:21]([CH3:22])[O:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 163764-nitro-1H-pyrazoleHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 24225555HCID 24225555, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-nitro-1H-pyrazole (Example 4-1d) (3.8 g, 34 mmol) in DMF (80 mL) cooled to 0° C., via an ice/water bath, was added t-BuOK (4.2 g, 38 mmol). After addition of the base the ice bath was removed and the mixture was stirred for 30 minutes followed by the addition of 4-(chloromethyl)-3,5-dimethylisoxazole (5 g, 34 mmol). The reaction was refluxed for 16 hours then cooled to ambient temperature. H2O was added to the reaction mixture and the precipitate formed was collected by filtration. The precipitate was washed with additional H2O then dried under high vacuum to afford 3,5-dimethyl-4-((4-nitro-1H-pyrazol-1-yl)methyl)isoxazole (5.8 g, 78%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz): 2.23 (s, 3H), 2.46 (s, 3H), 5.08 (s, 2H), 8.02 (s, 1H), 8.08 (s, 1H).

Workup

  1. customwas removed
  2. temperatureThe reaction was refluxed for 16 hours
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. washThe precipitate was washed with additional H2O
  6. customthen dried under high vacuum

Sources & evidence

ORD record
ord-b095e0a1511c4f59adedb0478625cc7d
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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