4-Bromobenzyl bromide → 1-(4-Bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

HRID 410332Notes

Reaction equation

HRID 410332 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[NH:19])=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>CC(=O)CC>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)[C:11]2=[NH:19])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 178509078HCID 178509078, compound

Product 1

HCID 462409921-(4-Bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamineYield 83.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (0.40 g, 1.40 mmol) in 2-butanone (30 ml) was added 4-bromobenzyl bromide (0.52 g, 2.1 mmol). The reaction was heated to 90° C. for 16 h. After this time, the resulting suspension was cooled to rt and filtered. The collected solid was washed with additional 2-butanone and then the solid was partitioned between dichloromethane and a saturated solution of NaHCO3. The biphasic mixture was stirred at rt for 10 min and then the organic layer was separated. The aqueous phase was extracted with additional dichloromethane and the combined organic fractions were washed with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine as a white solid (0.532 g, 83%). HPLC-MS 454, 456 [M+1]+.

Workup

  1. temperatureAfter this time, the resulting suspension was cooled to rt
  2. filtrationfiltered
  3. washThe collected solid was washed with additional 2-butanone
  4. customthe solid was partitioned between dichloromethane
  5. customthe organic layer was separated
  6. extractionThe aqueous phase was extracted with additional dichloromethane
  7. washthe combined organic fractions were washed with H2O
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84e7187ae7664f348bcdf5e6667a0c13
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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