Hydrochloric Acid → HCID 67272164, compound

HRID 1698568Notes

Reaction equation

HRID 1698568 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>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 22745204HCID 22745204, compoundHCID 178418443HCID 178418443, compound2×

Product 1

HCID 67272164HCID 67272164, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (513 mg, 2.67 mmol) in tetrahydrofuran (5 mL) was added 3M solution of ethyl magnesium bromide in diethyl ether (3.6 ml, 10.7 mmol), and the mixture was stirred at room temperature for 1 hour and refluxed for 20 hours. Addition of 3M solution of ethyl magnesium bromide in diethyl ether (5.3 mL, 16.0 mmol) was followed by refluxing for 30 hours. The reaction mixture was acidified with 6 N hydrochloric acid and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The resulting solid was washed with diisopropyl ether to give 440 mg (2.00 mmol, 74.8%) of the title compound.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureby refluxing for 30 hours
  3. extractionextracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-11e110a3290a46d4adf681b99dd37144
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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