Hydrochloric Acid → HCID 67272164, compound

HRID 1628380Notes

Reaction equation

HRID 1628380 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13]C)=O)[C:4]=2[NH:3]1.[CH2:15]([Mg]Br)[CH3:16].[CH2:19](OCC)[CH3:20].Cl>O1CCCC1.CO>[CH2:19]([C:11]([C:10]1[C:4]2[NH:3][C:2](=[O:1])[NH:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)([OH:13])[CH2:15][CH3:16])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22745204HCID 22745204, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67272164HCID 67272164, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (35.9 g, 189 mmol) in tetrahydrofuran (700 mL) was added dropwise 3M solution of ethylmagnesium bromide in diethyl ether (374 mL, 1.12 mol), and the mixture was refluxed for 3 hr. After cooling, methanol (70 mL) was added dropwise at 0° C., and 1 N hydrochloric acid (1300 mL) was added at 0° C. The mixture was stirred at room temperature for 40 min, and the organic layer was seated and concentrated in vacuo. The aqueous layer was extracted with ethyl acetate (400 mL×2). The combined organic layer was concentrated in vacuo. The resulting solid was suspended in diisopropyl ether (70 mL)-water (10 mL)-ethyl acetate (40 mL), and the mixture was refluxed for 30 min. After cooling to room temperature, the resulting solid was collected by filtration and washed with diisopropyl ether to give the title compound (33.0 g, 150 mmol, 79%) as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. concentrationconcentrated in vacuo
  4. extractionThe aqueous layer was extracted with ethyl acetate (400 mL×2)
  5. concentrationThe combined organic layer was concentrated in vacuo
  6. temperaturethe mixture was refluxed for 30 min
  7. temperatureAfter cooling to room temperature
  8. filtrationthe resulting solid was collected by filtration
  9. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-ca1c5cf395b44618a56191d61bb41a2c
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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