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Chlorosuccinimide → Isopropyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1698572
Notes
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Reaction equation

HRID 1698572 reaction equation
[CH:1]([O:4][C:5](=[O:22])[CH2:6][N:7]1[C:11]2[C:12]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]1=[O:21])([CH3:3])[CH3:2].[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].N(C(C)(C)C#N)=NC(C)(C)C#N>[CH:1]([O:4][C:5](=[O:22])[CH2:6][N:7]1[C:11]2[C:12]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][CH:14]=[C:15]([Cl:23])[C:10]=2[NH:9][C:8]1=[O:21])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 86632855Isopropyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

Product 1

HCID 86632856Isopropyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetateYield 65%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalyst
HCID 5943
Carbon Tetrachloride
Solvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of isopropyl[7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate (5.29 g, 17.4 mmol) in carbon tetrachloride (350 mL) was added N-chlorosuccinimide (2.55 g, 19.1 mmol) and 2,2′-azobisisobutyronitrile (86 mg, 0.522 mmol), and the mixture was stirred at 70° C. for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with dichloromethane (X2). The combined organic layer was washed with water (X1) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-50% ethyl acetate/hexane gradient mixture to give 3.83 g (11.3 mmol, 65.0%) of the title compound as a colorless solid.

Workup

  1. extractionextracted with dichloromethane (X2)
  2. washThe combined organic layer was washed with water (X1) and brine (X1)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 10-50% ethyl acetate/hexane gradient mixture

Sources & evidence

ORD record
ord-5c11c799a533448cbc62c47839faa704
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163935B2

Reaction notes

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