Water → 3-(4-Methyl-1H-imidazol-1-YL)-5-(trifluoromethyl)benzonitrile

HRID 505920Notes

Reaction equation

HRID 505920 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].F[C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[C:13]#[N:14].O>CN1CCCC1=O>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:10]2[CH:17]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:15]=[C:12]([CH:11]=2)[C:13]#[N:14])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5190373-Fluoro-5-(trifluoromethyl)benzonitrileHCID 178418800HCID 178418800, compound

Product 1

HCID 469003933-(4-Methyl-1H-imidazol-1-YL)-5-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Conditions

Temperature
22.5 °C

Procedure

A solution of 4-methyl-1H-imidazole (1.98 g, 24.11 mmol) in N-methylpyrrolidinone (NMP) (18 mL) is added to a solution of sodium hydride (0.82 g, 60%, 20.5 mmol) in NMP (18 mL) at 20-25° C. under an atmosphere of nitrogen. The mixture is stirred for 1 hour, before a solution of 3-fluoro-5-trifluoromethyl benzonitrile (XXI) (3.2 g, 16.4 mmol) in NMP (8 mL) is added. The reaction mixture is stirred for 2 hours at 20-25° C. and then water (120 mL) is added within 20 minutes and the resulting suspension is stirred for 16 hours.

Workup

  1. additionis added
  2. stirringthe resulting suspension is stirred for 16 hours

Sources & evidence

ORD record
ord-8b3e26381594479c995e7b0e340e0bbd
Source dataset
uspto-grants-2010_08
Patent number
US07781597B2

Reaction notes

Loading…