Potassium Carbonate → 4-Chloro-2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole

HRID 1698559Notes

Reaction equation

HRID 1698559 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([Cl:12])[C:4]=2[N:3]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:12][C:11]1[C:4]2[N:3]=[C:2]([O:27][C:20]3[C:21]([CH3:26])=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=3[Cl:18])[N:6]([CH3:7])[C:5]=2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate3×HCID 152922,4-Dichloro-6-methylphenol3×HCID 672730252,4-Dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole

Product 1

HCID 119482864-Chloro-2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazoleYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2,4-dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole (5.5 g, 20.2 mmol), 2,4-dichloro-6-methylphenol (10 g, 56.5 mmol) and potassium carbonate (8.4 g, 60.8 mmol) in N,N-dimethylformamide (55 mL) was heated at 100° C. for 9 h. To the mixture was added 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol) and potassium carbonate (4.2 g, 30.4 mmol) and heated at 100° C. for 16 h. Additional 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol) and potassium carbonate (4.2 g, 30.4 mmol) were added and heated at 100° C. for 9 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH silica gel eluting with a 12.5% ethyl acetate/n-hexane. The resulting solids were recrystallized from a 10% ethyl acetate/n-hexane to give 5.3 g (64%) of the title compound as a colorless crystal.

Workup

  1. temperatureheated at 100° C. for 9 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on NH silica gel eluting with a 12.5% ethyl acetate/n-hexane
  9. customThe resulting solids were recrystallized from a 10% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e25d4cfab0804f97aa3f5ff1b4bb6689
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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