Azobisisobutyronitrile → Methyl 7-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

HRID 1698576Notes

Reaction equation

HRID 1698576 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:15].[Cl:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:16][C:10]1[C:5]2[NH:4][C:3](=[O:15])[N:2]([CH3:1])[C:6]=2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 59635373methyl 1-methyl-2-oxo-1,3-dihydro-2H-benzimidazole-7-carboxylate

Product 1

HCID 67272570Methyl 7-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylateYield 29%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (500 mg, 2.42 mmol), N-chlorosuccinimide (355 mg, 2.66 mmol) and 2,2′-azobis(isobutyronitrile) (20 mg, 0.12 mmol) in carbon tetrachloride (40 mL) was refluxed for 2 days. After cooling, the reaction mixture was concentrated in vacuo. The resultant was extracted with ethyl acetate and water. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on a silica gel to give 167 mg (0.07 mmol, 29%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionThe resultant was extracted with ethyl acetate and water
  4. dry with materialThe organics was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-bfa2ff9796f0418781491b727e3674ff
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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