Chlorosuccinimide → 4-Chloro-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698556Notes

Reaction equation

HRID 1698556 reaction equation
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=[O:15])[NH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[Cl:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:17][C:9]1[C:10]2[NH:14][C:13](=[O:15])[N:12]([CH3:16])[C:11]=2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 672726137-(1-Ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 672724674-Chloro-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneYield 68%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

2,2′-Azobisisobutyronitrile (AIBN) (94 mg, 0.57 mmol) was added to a mixture of 7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (2.90 g, 13.3 mmol) and N-chlorosuccinimide (1.95 g, 14.6 mmol) in carbon tetrachloride (250 mL). The mixture was stirred at 70° C. for 2 days. The reaction was concentrated in vacuo, extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to give residue. The residue was crystallized from ethanol/iso-propanol to afford the title compound as colorless crystals (2.28 g, 68%). mp 165-166° C.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give residue
  8. customThe residue was crystallized from ethanol/iso-propanol

Sources & evidence

ORD record
ord-23e8f81a18d84dd58a0e0a6f8822cad7
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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