Sodium hydride → 2-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole

HRID 2081843

Reaction equation

HRID 2081843 reaction equation
[CH2:1]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15]Cl>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:15][C:14]2[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:13]=2[Cl:12])[CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 118153512-butyl-1H-imidazole

Product 1

HCID 199367742-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-n-butylimidazole (3.75 g, 0.03 mol) in dry dimethylformamide (4 mL) was added to sodium hydride (0.95 g) in dimethylformamide (18 mL). After the gas evolution subsided, the mixture was stirred one hour under argon and 2-chloro-6-fluorobenzylchloride (5.5. g, 0.031 mol) in dimethylformamide (7 mL) was added to produce an exotherm. The mixture was stirred for 17 hours at ambient temperature, diluted with ice water and extracted with ethyl acetate. The washed, dried, concentrated organic layer provided 7.63 (94%) of the title compound whose NMR was consistent with the structure. This material was used without further purification.

Workup

  1. customto produce an exotherm
  2. stirringThe mixture was stirred for 17 hours at ambient temperature
  3. extractionextracted with ethyl acetate
  4. customThe washed, dried

Sources & evidence

ORD record
ord-fd412f58508e4a279cf9b50a39bdcbee
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Linked notes

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