Dimethylformamide → HCID 15870528, compound

HRID 609766Notes

Reaction equation

HRID 609766 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[CH2:37](Br)[CH:38]=[CH2:39]>CCCCCC.ClCCl.O>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:39][CH:38]=[CH2:37])[CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 15870527HCID 15870527, compound

Product 1

HCID 15870528HCID 15870528, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226440Methylenechloride HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To 0.66 g of 1-benzyl-6-chloro-2-(indol-5-ylaminocarbonyl)benzimidazole was added 50 ml of dimethylformamide, further added 170 mg of oily sodium hydride, said mixture was stirred under nitrogen gas atmosphere at 60° C. for 1 hour. Under cooling at 0° C., 0.14 ml of allyl bromide was added to the reaction mixture, and stirred at room temperature overnight, then water was added thereto and extracted with ethyl acetate, the extract was washed with water and an aqueous solution saturated with sodium chloride. The washed extract was dried with anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: 10% n-hexane/dichloromethane), recrystallized from ethyl acetate-ethanol, there was obtained 0.35 g of 1-benzyl-6-chloro-2-(1-allylindol-5-ylaminocarbonyl)benzimidazole as in the form of colorless needle crystals.

Workup

  1. temperatureUnder cooling at 0° C.
  2. stirringstirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water
  5. extractionThe washed extract
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customrecrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-71cbed95909742cabb84616efe61f0c9
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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