Hydrochloric Acid → HCID 59145911, compound

HRID 887760Notes

Reaction equation

HRID 887760 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([CH2:23][CH2:24]C(OC)=O)=[C:18]([C:19]([O:21]C)=O)[C:13]=2[N:12]=[C:11]1[CH3:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[OH-].[Na+]>O1CCCC1.CO>[CH2:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]3[CH2:23][CH2:24][C:19](=[O:21])[C:18]=3[C:13]=2[N:12]=[C:11]1[CH3:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 59145924HCID 59145924, compound

Product 1

HCID 59145911HCID 59145911, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

To a suspension of 60% sodium hydride (33 mg, 0.81 mmol) in tetrahydrofuran (5 mL) were added a solution of methyl 1-benzyl-5-(3-methoxy-3-oxopropyl)-2-methyl-1H-benzimidazole-4-carboxylate (148 mg, 0.40 mmol) in tetrahydrofuran (3 mL) and methanol (1 drop), and the mixture was heated under reflux for 2.5 hr. The reaction solution was concentrated to dryness to give yellow-brown crystals. The obtained crystals were gradually added to 12M hydrochloric acid (3 mL) heated to 100° C., and the mixture was stirred for 2 hr. The reaction solution was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (62 mg, yield 56%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hr
  3. concentrationThe reaction solution was concentrated to dryness
  4. customto give yellow-brown crystals
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43fbab99e37d42a09b40c13c4b48d377
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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