Dichloromethane → HCID 178432177, compound

HRID 991592Notes

Reaction equation

HRID 991592 reaction equation
[OH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([CH3:24])[C:16]=1[CH2:17]Br.C(Cl)Cl>C(#N)C.O>[CH3:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([CH3:24])[C:16]=1[CH2:17][O:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzeneHCID 178432174HCID 178432174, compound

Product 1

HCID 178432177HCID 178432177, compoundYield 6.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

4-hydroxy -2-methylbenzimidazole (0.57 g, 3.8 mmol) was dissolved in acetonitrile (4 ml). To the solution were added sodium hydroxide (0.17 g, 43 mmol) (dissolved in 1 ml water) and 2,6-dimethyl-4-fluorobenzylbromide (0.82 g, 3.8 mmol) dissolved in acetonitrile (6 ml) and the reaction mixture was refluxed for 80 min. and was stirred for 20 h. at ambient temperature. To the reaction mixture was added methylene chloride (25 ml) and water (25 ml). The organic layer was separated, washed three times with 2 M NaOH, dried over sodium sulfate and was evaporated under reduced pressure. The residue was crystallized from ethyl acetate and was then purified twice by column chromatography on silica gel a) methylene chloride: methanol (10:1) b) ethyl acetate: methanol:acetic acid: water (96:6:6:4). There was obtained 0.066 g (6%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 80 min.
  2. customThe organic layer was separated
  3. washwashed three times with 2 M NaOH
  4. dry with materialdried over sodium sulfate
  5. customwas evaporated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate
  7. customwas then purified twice by column chromatography on silica gel a) methylene chloride: methanol (10:1) b) ethyl acetate: methanol:acetic acid: water (96:6:6:4)

Sources & evidence

ORD record
ord-69bdd13022e646419cb80c07c329d708
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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