Benzyl Bromide → HCID 22402944, compound

HRID 259711Notes

Reaction equation

HRID 259711 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[C:7](=[CH:9][CH:10]=[C:11]([C:17]([O:19][CH3:20])=[O:18])[C:12]=2[C:13]([O:15][CH3:16])=[O:14])[N:8]=1.[H][H].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([N:8]1[C:7]2=[CH:9][CH:10]=[C:11]([C:17]([O:19][CH3:20])=[O:18])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:6]2[N:5]=[C:4]1[CH3:3])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178497326HCID 178497326, compound

Product 1

HCID 22402944HCID 22402944, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.750 g, 80% oil dispersion, 25.0 mmol) is added, in portions, to a solution of dimethyl 2-methyl-4,5-benzimidazoledicarboxylate (6.07 g, 24.6 mmol) in dry dimethylformamide at 0° C. with stirring. After evolution of hydrogen ceases, benzyl bromide (2.93 mL, 24.6 mmol) is added to the reaction mixture and stirring is continued for 16 hours. The reaction mixture is concentrated in vacuo and the resultant residue is dispersed in methylene chloride and water. The phases are separated and the aqueous phase is extracted with methylene chloride. The organic phases are combined, dried and concentrated in vacuo to afford a solid residue. Recrystallization of the solid from ethyl acetate affords the title product as an off-white powder (3.81 g, 45.0%), mp 192°-195° C.

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additionthe resultant residue is dispersed in methylene chloride
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with methylene chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto afford a solid residue
  9. customRecrystallization of the solid from ethyl acetate

Sources & evidence

ORD record
ord-6064342c0f1d4f7a984c027912ee1b4d
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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