Dimethylformamide → HCID 58306803, compound

HRID 1909891Notes

Reaction equation

HRID 1909891 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([NH:12][CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Cl:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1>O>[Cl:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[C:10]([NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[O:11])=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 66868084HCID 66868084, compound

Product 1

HCID 58306803HCID 58306803, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 4-{[(1H-benzimidazol-2-ylcarbonyl)amino]methyl}benzoate (230 mg), potassium carbonate (257 mg), and DMF (4.6 mL) was added p-chlorobenzylbromide (191 mg), followed by stirring at room temperature for 2.5 days. To the reaction mixture was added water (30 mL), followed by extraction with ethyl acetate (30 mL). The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After filtration and concentration, the obtained residue was washed with methanol (2 mL) to obtain methyl 4-[({[1-(4-chlorobenzyl)-1H-benzimidazol-2-yl]carbonyl}amino)methyl]benzoate (269 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (30 mL)
  2. washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. washthe obtained residue was washed with methanol (2 mL)

Sources & evidence

ORD record
ord-8cfdaa3e1a6f4736ae837020dee6d06d
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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