Chloroform → HCID 67211258, compound

HRID 452147Notes

Reaction equation

HRID 452147 reaction equation
OCC[C:4]1[N:8]([CH2:9][C:10]2[CH:27]=[CH:26][C:13]3/[C:14](=[CH:23]/[C:24]#[N:25])/[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]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:30]=[C:31]([CH3:32])[C:6]=2[N:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:32][C:31]1[C:6]2[N:5]=[CH:4][N:8]([CH2:9][C:10]3[CH:27]=[CH:26][C:13]4/[C:14](=[CH:23]/[C:24]#[N:25])/[C:15]5[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=5[CH2:17][CH2:18][C:12]=4[CH:11]=3)[C:7]=2[CH:28]=[C:29]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:30]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67210425HCID 67210425, compound

Product 1

HCID 67211258HCID 67211258, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[step 1] (E)-{2-[2-(2-Hydroxyethyl)-4-methyl-6-phenylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile (100 mg, 0.20 mmol) obtained in Example 59, step 1 was dissolved in acetonitrile (2 mL), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (128 mg, 0.30 mmol) was added, and the mixture was stirred at room temperature for 4 hr. Chloroform (20 mL) and saturated aqueous sodium hydrogen carbonate solution (20 mL) were added to the mixture, and the mixture was stirred at room temperature for 30 min. 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=100/0 to 95/15) to give (E)-[2-(4-methyl-6-phenylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (14 mg, 15%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/15)

Sources & evidence

ORD record
ord-acf1c3bb3d5b49718304ff6ca701a053
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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