Hydrochloric Acid → (E)-[2-(6-Carboxy-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 452182Notes

Reaction equation

HRID 452182 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:36])[C:8]2[N:12]=[C:11]([CH2:13][CH2:14][CH3:15])[N:10]([CH2:16][C:17]3[CH:34]=[CH:33][C:20]4/[C:21](=[CH:30]/[C:31]#[N:32])/[C:22]5[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=5[CH2:24][CH2:25][C:19]=4[CH:18]=3)[C:9]=2[CH:35]=1)=[O:4].[OH-].[Na+].Cl>C(O)C>[C:3]([C:5]1[CH:6]=[C:7]([CH3:36])[C:8]2[N:12]=[C:11]([CH2:13][CH2:14][CH3:15])[N:10]([CH2:16][C:17]3[CH:34]=[CH:33][C:20]4/[C:21](=[CH:30]/[C:31]#[N:32])/[C:22]5[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=5[CH2:24][CH2:25][C:19]=4[CH:18]=3)[C:9]=2[CH:35]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67210309(E)-[2-(6-methoxycarbonyl-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

Product 1

HCID 67211448(E)-[2-(6-Carboxy-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrileYield 114.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[step 2] (E)-[2-(6-Methoxycarbonyl-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (500 mg, 1.05 mmol) obtained in step 1 was dissolved in ethanol (7.5 mL), 2 mol/L aqueous sodium hydroxide solution (2.5 mL) was added, and the mixture was stirred under reflux for 30 min. The mixture was adjusted to pH 2 with 2 mol/L hydrochloric acid, and the precipitated solid was collected by filtration to give the title compound (554 mg) quantitatively.

Workup

  1. temperatureunder reflux for 30 min
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-08182144f0aa46d2b6117fe3f5893158
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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