Dimethylformamide → HCID 86684868, compound

HRID 238366Notes

Reaction equation

HRID 238366 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[CH3:8][N:9]1[C:13]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=[N:10]1.CI>O>[CH3:3][N:14]([C:13]1[N:9]([CH3:8])[N:10]=[CH:11][CH:12]=1)[C:15](=[O:26])[C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86684867HCID 86684867, compound

Product 1

HCID 86684868HCID 86684868, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under cooling in an ice bath, 60% sodium hydride (39 mg) was added to a dimethylformamide (2.1 mL) solution of N-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)benzamide (200 mg), and the obtained solution was then stirred for 20 minutes. Thereafter, methyl iodide (51 μL) was added to the reaction solution, and the obtained solution was then stirred for 1.5 hours, and then at a room temperature for 17 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50), so as to obtain the title compound (141 mg) in the form of a colorless oily substance. 1H NMR (200 MHz, CHLOROFORM-d) δ ppm 3.41 (s, 3H) 3.60 (s, 3H) 6.01 (d, J=1.76 Hz, 1H) 7.36 (d, J=1.76 Hz, 1H) 7.43 (d, J=8.79 Hz, 2H) 7.52 (d, J=8.35 Hz, 2H)

Workup

  1. temperatureUnder cooling in an ice bath
  2. stirringthe obtained solution was then stirred for 1.5 hours
  3. waitat a room temperature for 17 hours
  4. extractionthe obtained mixture was then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  7. concentrationfollowed by vacuum concentration
  8. customThe residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50)

Sources & evidence

ORD record
ord-f3c591f01cac44a7a9b59872ace95d03
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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