Sodium Hydroxide → HCID 67211111, compound

HRID 452148Notes

Reaction equation

HRID 452148 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]3/[C:17](=[CH:26]/[C:27]#[N:28])/[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH2:20][CH2:21][C:15]=3[CH:14]=2)[C:10]2[CH:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:33]=[C:34]([CH3:35])[C:9]=2[N:8]=1)=[O:4].[OH-].[Na+]>C(O)C>[C:3]([CH2:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]3/[C:17](=[CH:26]/[C:27]#[N:28])/[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH2:20][CH2:21][C:15]=3[CH:14]=2)[C:10]2[CH:31]=[C:32]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:33]=[C:34]([CH3:35])[C:9]=2[N:8]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67210402HCID 67210402, compound

Product 1

HCID 67211111HCID 67211111, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[step 1] (E)-{2-[2-(2-Methoxycarbonylethyl)-4-methyl-6-phenylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile (350 mg, 0.65 mmol) obtained in Example 61, step 1 was dissolved in ethanol (4 mL), 2 mol/L aqueous sodium hydroxide solution (0.8 mL) was added, and the mixture was stirred at room temperature for 2 hr. The mixture was concentrated under reduced pressure, water and 2 mol/L hydrochloric acid were added, and the precipitate was collected by filtration to give (E)-[2-{2-(2-carboxyethyl)-4-methyl-6-phenylbenzimidazol-1-yl}methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (336 mg, 99%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, water and 2 mol/L hydrochloric acid
  2. additionwere added
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7f3b4abe35d748aabe64961fd48c25cb
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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