Hydrochloric Acid → HCID 67211673, compound

HRID 452127Notes

Reaction equation

HRID 452127 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:27]=[CH:26][C:13]3/[C:14](=C/C#N)/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH2:2][CH3:3].[OH-:32].[Na+].Cl.[CH2:35]([OH:37])[CH3:36]>>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:27]=[CH:26][C:13]3/[C:14](=[CH:36]/[C:35]([OH:32])=[O:37])/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 67211720HCID 67211720, compound

Product 1

HCID 67211673HCID 67211673, compoundYield 89%

Procedure

(E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (260 mg, 0.64 mmol) obtained in Example 1 was dissolved in ethanol (2.5 mL), 10 mol/L aqueous sodium hydroxide solution (1 mL) was added, and the mixture was stirred under reflux for 24 hr. The mixture was neutralized with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=90/10) to give the title compound (compound 2) (243 mg, 89%).

Workup

  1. temperatureunder reflux for 24 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=90/10)

Sources & evidence

ORD record
ord-17524fbff8b54cb78a2b8657c5b1cca2
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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