HCID 178497355, compound → HCID 178490008, compound

HRID 1278725Notes

Reaction equation

HRID 1278725 reaction equation
C[O:2][C:3]([C:5]1[CH:25]=[CH:24][C:8]2[NH:9][C:10]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4]>CO.[OH-].[Na+]>[CH3:23][O:22][C:16]1[CH:15]=[C:14](/[CH:13]=[CH:12]/[C:10]2[NH:9][C:8]3[CH:24]=[CH:25][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

4

Reactant 1

HCID 178497355HCID 178497355, compound

Product 1

HCID 178490008HCID 178490008, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-[2-(3,4-Dimethoxyphenyl)-vinyl]-1H-benzoimidazole-5-carboxylic acid methyl ester (3.5 g; 11 mmol) in MeOH (75 mL) and 2.5N NaOH solution (7.5 mL) was refluxed for 3 hours. The reaction mixture was cooled to ambient temperature and stirred for 18 hours. The reaction mixture was concentrated to dryness. The residue was dissolved in H2O, and acidified with 2N HCl. Precipitate was collected. Recrystallization from MeOH gave 600 mg (15%) of the title compound as creamy solid, mono-hydrochloride, m.p. over 285° C. Anal. Calcd. for C18H16N2O4HCl: C, 59.92, H, 4.75; N, 7.76. Found: C, 59.62; H, 4.80; N, 7.66. Mass spectrum: (EI; M+) m/z 324. 1H-NMR (DMSO-d6; 400 MHz) δ13.5(broad s, 1H), 8.24 (d, 1H), 8.14-8.2 (d, 1H), 8.02-8.06 (dd, 1H), 7.8 (d, 1H), 7.34 (d 1H), 7.26-7.28 (dd, 1H), 7.2-7.24 (d, 1H), 7.1 (d, 1H), 3.87 (s, 3H), 3.83 ppm (s, 3H).

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionThe residue was dissolved in H2O
  4. customPrecipitate was collected
  5. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-91a92bb8f3484308ac2b266f1c4c1415
Source dataset
uspto-grants-2002_09
Patent number
US06444694B1

Reaction notes

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