2-Hydroxy benzimidazole → 1-[4,4-Bis(4-fluorophenyl)butyl]-1,3-dihydro-benzoimidazol-2-one

HRID 1804867Notes

Reaction equation

HRID 1804867 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[O:12].[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH2:23]Cl)=[CH:16][CH:15]=1>CN(C=O)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH2:21][CH2:22][CH2:23][N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][C:4]2=[O:12])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 119852-Hydroxy benzimidazoleHCID 24758Sodium hydrideHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)

Product 1

HCID 247381691-[4,4-Bis(4-fluorophenyl)butyl]-1,3-dihydro-benzoimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (0.72 g, 18 mmol) in DMF (15.0 mL) was added a solution of 1,3-dihydro-benzoimidazol-2-one (11) (2.6 g, 20.0 mmol, Aldrich) in DMF (10.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and a solution of compound 2 (2.8 g, 10 mmol) in DMF (10.0 mL) was added. The resulting mixture was stirred at 60° C. for 4 hours. After this period, the mixture was cooled to room temperature and quenched with water (20 mL). The mixture was extracted with ethyl acetate (100 mL×3). The organic layer was dried with anhydrous Na2SO4 and concentrated to give a crude sample. The crude sample was purified by column chromatography using ethyl acetate/hexane gradient as an eluent to give the title compound 12. MS: m/z 379. 1H NMR (CDCl3): δ 9.41 (s, 1H), 7.10 (m, 8H), 6.92 (t, J=8 Hz, 4H), 3.93 (m, 3H), 2.07 (m, 2H), 1.73 (m, 2H).

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 4 hours
  2. waitAfter this period
  3. temperaturethe mixture was cooled to room temperature
  4. customquenched with water (20 mL)
  5. extractionThe mixture was extracted with ethyl acetate (100 mL×3)
  6. dry with materialThe organic layer was dried with anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto give a crude sample
  9. customThe crude sample was purified by column chromatography

Sources & evidence

ORD record
ord-442395d69b5747c5944062ebc40bd048
Source dataset
uspto-grants-2013_01
Patent number
US08354434B2

Reaction notes

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