2-Chloro-N,N-dimethylethylamine → HCID 14371284, compound

HRID 476891Notes

Reaction equation

HRID 476891 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:3]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4].[H-].[Na+].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25]Cl>CS(C)=O.C(Cl)(Cl)Cl>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][N:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=[C:5]1[C:3]([N:2]([CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:4]

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 14371283HCID 14371283, compound

Product 1

HCID 14371284HCID 14371284, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Procedure

N-Methyl-N-(2-pyridyl)benzimidazole-2-carboxamide (1.0 g) prepared in Example 5 was dissolved in dry DMSO (20 ml), 60% sodium hydride (0.17 g) was added and stirred at room temperature for 1 hr in an argon atmosphere. Excess β-dimethylaminoethyl chloride was added to the mixture and reacted at room temperature under agitation for 20 hrs. The reaction solution was diluted with chloroform, washed with water, dried over anhydrous Na2SO4 and the solvent was distilled off. Purification of the residue by column chromatography on silica gel (using silica gel manufactured by Merck Co., Ltd.) gave the title compound (0.88 g) as an oily product.

Workup

  1. customreacted at room temperature under agitation for 20 hrs
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. distillationthe solvent was distilled off
  5. customPurification of the residue by column chromatography on silica gel (using silica gel manufactured by Merck Co., Ltd.)

Sources & evidence

ORD record
ord-78cda554a28a416a936f1434237ffc77
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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