Methyl chloroacetate → HCID 19963012, compound

HRID 52149Notes

Reaction equation

HRID 52149 reaction equation
[CH3:1][C:2]1[C:3]([CH2:19][S:20][C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[N:22]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1[C:3]([CH2:19][S:20][C:21]2[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:31][C:32]([O:34][CH3:35])=[O:33]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 199630842-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole

Product 1

HCID 19963012HCID 19963012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole (2 g) was dissolved in dimethylformamide and reacted with methyl chloroacetate (0.45 ml) in the presence of potassium carbonate (0.71 g) at 50°-60° C. After the completion of the reaction, the dimethylformamide was distilled away and the residue was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give an oily product. The oily product was purified by column chromatography to give 2-((3-methyl-4-(2-(N-benzyl-N-methoxycarbonylmethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe dimethylformamide was distilled away
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away
  6. customto give an oily product
  7. customThe oily product was purified by column chromatography

Sources & evidence

ORD record
ord-358770dc8b62426c8b8107acc0b2f1eb
Source dataset
uspto-grants-1997_04
Patent number
US05616581

Reaction notes

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