2-Imidazolidinone → HCID 24737864, compound

HRID 1804866Notes

Reaction equation

HRID 1804866 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:17][CH2:18][CH2:19]Cl)=[CH:12][CH:11]=1>CN(C=O)C>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[CH2:17][CH2:18][CH2:19][N:3]2[CH2:7][CH2:6][NH:5][C:4]2=[O:8])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 84532-ImidazolidinoneHCID 24758Sodium hydrideHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)

Product 1

HCID 24737864HCID 24737864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (0.72 g, 18 mmol) in DMF (20.0 mL) was added a solution of imidazolidin-2-one (1) (2.5 g, 30.0 mmol, Aldrich) in DMF (10.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 45 minutes and then a solution of 4,4-bis(4-fluorophenyl)butyl chloride (2) (5.6 g, 10 mmol) in DMF (10.0 mL) was added. Then the 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 3. MS: m/z 331. 1H NMR (CDCl3): δ 7.16 (m, 4H), 6.96 (t, J=8 Hz, 4H), 4.36 (br, 1H), 3.91 (t, J=8 Hz, 1H), 3.38 (m, 2H), 3.32 (m, 2H), 3.21 (t, J=8 Hz, 2H), 2.00 (dd, J=8, 12 Hz, 2H), 1.45 (m, 2H).

Workup

  1. stirringThen the 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-42e8df09a32f4d06b4296b998c1084ed
Source dataset
uspto-grants-2013_01
Patent number
US08354434B2

Reaction notes

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