Sodium hydride → HCID 66986886, compound

HRID 555728Notes

Reaction equation

HRID 555728 reaction equation
Cl.[CH3:2][C:3]1[NH:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.[H-].[Na+]>CN(C=O)C>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:4]2[CH:5]=[C:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:7]=[C:3]2[CH3:2])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 178432486HCID 178432486, compound

Product 1

HCID 66986886HCID 66986886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-4-phenyl-1H-imidazole HCl salt (1.51 g, 7.75 mmol), 4-chlorobenzyl bromide (1.75 g, 8.53 mmol) and NaH (745 mg, 18.6 mmol) in DMF (20 mL) is stirred at RT. After completion the reaction mixture is quenched by H2O. EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; ES-MS: M+=283.1: At Ret=3.93 min.

Workup

  1. customAfter completion the reaction mixture is quenched by H2O
  2. additionEtOAc is added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-88580e86a4ed40fdaaba56bed19b67ef
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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