Hydrochloric Acid → HCID 59497268, compound

HRID 1747290Notes

Reaction equation

HRID 1747290 reaction equation
C([O:3][C:4](=[O:28])/[CH:5]=[CH:6]/[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:8]1=[O:27])C.[OH-].[Na+].Cl>CO>[C:17]1([CH2:16][N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7](/[CH:6]=[CH:5]/[C:4]([OH:28])=[O:3])[C:8]2=[O:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59497305HCID 59497305, compound

Product 1

HCID 59497268HCID 59497268, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-acrylic acid ethyl ester (0.1 g, 0.30 mmol) in MeOH (10 mL) was added 2N NaOH (5 mL). The reaction mixture was stirred at room temperature for 3 h. Since the mixture was heterogeneous, the mixture was heated to 60° C. for 2 h. The reaction mixture was then treated with 1N HCl and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1 CH2Cl2:MeOH as an eluent to afford 30 mg of the title compound as an off-white solid. LCMS (ESMS): m/z 345.12 (M+H+).

Workup

  1. temperaturethe mixture was heated to 60° C. for 2 h
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-878ba3061d494026a84737896c09fb41
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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