Methyl chloroacetate → HCID 19963012, compound

HRID 1720053Notes

Reaction equation

HRID 1720053 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-b8a99f97879e4088a3f91cf13a17bc65
Source dataset
uspto-grants-1996_04
Patent number
US05504082

Reaction notes

Loading…