Imidazole → HCID 118555065, compound

HRID 1051286Notes

Reaction equation

HRID 1051286 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.F[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]#[N:13].O>CS(C)=O>[N:3]1([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=2[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]#[N:13])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 43657400HCID 43657400, compound

Product 1

HCID 118555065HCID 118555065, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A reaction mixture solution prepared by suspending 41.1 mg of 3-fluoro-4-hydroxybenzonitrile, 33.4 mg of isobutyl bromide and 62.2 mg of potassium carbonate in 1 mL of dimethylformamide was heated at 110° C. for 5 hours under a nitrogen atmosphere. After the addition of water to the reaction mixture solution, extraction was performed using ethyl acetate. The organic layer was washed with saline, followed by drying and concentrating under reduced pressure to obtain a crude product of 3-fluoro-4-(2-methylpropoxy)benzonitrile. (2) A reaction mixture prepared by adding 15.7 mg of sodium hydride and 24.5 mg of imidazole to the crude product of 3-fluoro-4-(2-methylpropoxy)benzonitrile obtained above and suspending the above in 1 mL of dimethylsulfoxide was heated at 110° C. for 5 hours under a nitrogen atmosphere. After the addition of water to the reaction mixture solution, extraction was performed using ethyl acetate. The organic layer was washed with saline, followed by drying and concentrating under reduced pressure to obtain a crude product of 3-(1H-imidazol-1-yl)-4-(2-methylpropoxy)benzonitrile.

Workup

  1. customobtained above and
  2. extractionto the reaction mixture solution, extraction
  3. washThe organic layer was washed with saline
  4. customby drying
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-3c5a2c9283f44cb196ee248c27918d77
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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