Ethyl chloroformate → ethyl 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole1-carboxylate

HRID 1720049Notes

Reaction equation

HRID 1720049 reaction equation
[CH3:1][C:2]1[C:3]([CH2:17][S:18][C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:28](Cl)(=[O:32])[O:29][CH2:30][CH3:31].[H-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[C:3]([CH2:17][S:18][C:19]2[N:20]([C:28]([O:29][CH2:30][CH3:31])=[O:32])[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 98492092-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

Product 1

HCID 15307532ethyl 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((3-Methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)- 1H-benzimidazole (10 g) was reacted with 1.1 equivalents of ethyl chlorocarbonate in dimethylformamide in the presence of 1.1 equivalents of sodium hydride at room temperature. After the completion of the reaction, the solvent was distilled away and water was added to the residue, followed by extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 11 g of ethyl 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)-methylthio)-1H-benzimidazole-1-carboxylate as crystals, melting point 145°-147° C.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled away
  3. additionwater was added to the residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-e20fad796d9b4679b3ab576ec8d7bb82
Source dataset
uspto-grants-1996_04
Patent number
US05504082

Reaction notes

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