Sodium Hydroxide → HCID 178489347, compound

HRID 2253314Notes

Reaction equation

HRID 2253314 reaction equation
C[O:2][C:3]([C:5]1[C:10]2[NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])=[N:13][C:9]=2[CH:8]=[CH:7][C:6]=1[CH:22](C(OCC)=O)[C:23]([O:25]CC)=[O:24])=[O:4].[OH-].[Na+]>C1COCC1.CO>[C:23]([CH2:22][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[NH:11][C:10]=2[C:5]=1[C:3]([OH:4])=[O:2])([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178472256HCID 178472256, compound

Product 1

HCID 178489347HCID 178489347, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diethyl [7-(methoxycarbonyl)-2-(2-methoxyphenyl)-1H-benzimidazol-6-yl]malonate (4.96 g, 11.3 mmol) and aqueous 2 N NaOH solution (50.0 mL, 100 mmol) in THF (112 mL) and MeOH (45 mL) was stirred at room temperature for 17 h. The mixture was concentrated under reduced pressure. The residual aqueous solution was cooled to 0° C. and aqueous 2 N HCl solution (50 mL) was slowly added (pH 4 obtained). The resulting suspension was heated at 70° C. for 15 h. The cooled suspension was filtered to give the title compound (3.72 g, 100% yield) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionaqueous 2 N HCl solution (50 mL) was slowly added
  3. custom(pH 4 obtained)
  4. temperatureThe resulting suspension was heated at 70° C. for 15 h
  5. filtrationThe cooled suspension was filtered

Sources & evidence

ORD record
ord-f5c48ce9555049319b9e4262ce71b38a
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

Loading…