2-Chloro-N,N-dimethylethylamine → 1-(beta-Dimethylaminoethyl)-N-(2-pyridyl)benzimidazole-2-carboxamide

HRID 476894

Reaction equation

HRID 476894 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[NH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:9].[H-].[Na+].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl.[Cl-].[NH4+]>CS(C)=O>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][N:14]1[C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[N:11]=[C:10]1[C:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 30872911H-Benzimidazole-2-carboxamide, N-2-pyridinyl-

Product 1

HCID 143712881-(beta-Dimethylaminoethyl)-N-(2-pyridyl)benzimidazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(2-pyridyl)benzimidazole-2-carboxamide (2.0 g) prepared in Example 1 was dissolved in dry DMSO (25 ml), sodium hydride (0.35 g) was added and stirred at room temperature for 1 hr. Excess β-dimethylaminoethyl chloride was added to the mixture and allowed to react overnight at room temperature under agitation. The reaction solution was poured into aqueous saturated ammonium chloride solution and extracted with chloroform. The chloroform layer was dried over anhydrous Na2SO4 and the solvent was distilled off. Purification of the residue by column chromatography on silica gel gave the title compound (0.84 g).

Workup

  1. customto react overnight at room temperature under agitation
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous Na2SO4
  4. distillationthe solvent was distilled off
  5. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-d86dc80316844185b931bc596695868e
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Linked notes

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