Water → HCID 10119952, compound

HRID 1181326Notes

Reaction equation

HRID 1181326 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=3)=[CH:23][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl.Cl[CH2:39][C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1.O>CN(C)C=O>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:39][C:40]4[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=4)[CH:29]=3)=[CH:25][CH:26]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10139190HCID 10139190, compound

Product 1

HCID 10119952HCID 10119952, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 1-cyclohexyl-2-[4-(3-hydroxyphenyloxy)phenyl]-benzimidazole-5-carboxylate (78 g) obtained in Example 28 was suspended in dimethylformamide (800 ml), and sodium hydride (60% oil, 14 g) was added under ice-cooling. The mixture was stirred for 1 hr at room temperature. After the reaction mixture was ice-cooled, 4-chloromethylpyridine hydrochloride (29 g) was added and the mixture was stirred for 30 min. The mixture was then stirred overnight at room temperature. Water was added to the reaction mixture and the precipitated crystals were collected by filtration. The resulting crystals were recrystallized from ethyl alcohol to give the title compound (77 g, yield 82%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringthe mixture was stirred for 30 min
  4. stirringThe mixture was then stirred overnight at room temperature
  5. filtrationthe precipitated crystals were collected by filtration
  6. customThe resulting crystals were recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-a92d3766aeb54b6cb296d77743c00dfc
Source dataset
uspto-grants-2007_10
Patent number
US07285551B2

Reaction notes

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