Hydrogen Peroxide → 2-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzamide

HRID 2218641Notes

Reaction equation

HRID 2218641 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]#[N:20])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=[O:26].[K+].[K+].OO>CS(C)=O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]([NH2:20])=[O:26])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 689329272-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzonitrile

Product 1

HCID 597703282-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzonitrile (100 mg, 0.32 mmol) in DMSO (3 mL) and add solid K2CO3 (50 mg) followed by 30% H2O2 (100□1). Stir the reaction for 3 h. and quench by pouring into water. Collect the white solid and dry in a vacuum oven to yield 84 mg (81%). 1H NMR (DMSO-d6) δ2.95 (br s, 2H), 3.38 (br s, 2H), 6.67-7.56 (m, 12H), 7.90 (s, 1H); MS (ES) 326 (M+1) (M−1). HPLC shows 95% purity.

Workup

  1. customthe reaction for 3 h.
  2. customquench
  3. additionby pouring into water
  4. customCollect the white solid
  5. customdry in a vacuum oven
  6. customto yield 84 mg (81%)

Sources & evidence

ORD record
ord-a27d2f163eb44c5783bf846971344ab1
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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