Dimethylformamide → HCID 19600543, compound

HRID 357583Notes

Reaction equation

HRID 357583 reaction equation
CO[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[C:8]=1[CH3:24].[H-].[Na+].[C:27](Cl)(=[O:31])[O:28][CH2:29][CH3:30].[Cl-].[NH4+].[CH3:35]N(C)C=O>>[CH2:29]([O:28][C:27]([N:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[N:16]=[C:15]1[S:14][CH2:13][C:9]1[C:8]([CH3:24])=[C:7]([O:6][CH2:5][CH2:4][CH2:3][CH3:35])[CH:12]=[CH:11][N:10]=1)=[O:31])[CH3:30]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 9949996Rabeprazole-thioether

Product 1

HCID 19600543HCID 19600543, compound

Procedure

0.8 g of 2-{4-(3-methoxypropoxy)-3-methylpyridine-2-yl}methylthio-1H-benzimidazole was dissolved in 10 ml of dimethylformamide to obtain a solution. 0.23 g of 60% sodium hydride was added to this solution at 0° C. The obtained mixture was stirred for 15 minutes. 0.4 g of ethyl chlorocarbonate was dropwise added to the resulting mixture at 0° C. The obtained mixture was stirred at a room temperature for one hour. A saturated aqueous solution of ammonium chloride was added to the resulting mixture to stop the reaction. The reaction mixture was extracted with chloroform. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain a residue. This residue was purified by silica gel column chromatography to obtain 0.82 g of the title compound as a white crystal.

Workup

  1. customto obtain a solution
  2. stirringThe obtained mixture was stirred at a room temperature for one hour
  3. customthe reaction
  4. extractionThe reaction mixture was extracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto obtain a residue
  9. customThis residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1a432dd2b074925949a47332c2eb116
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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