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

HRID 1698608
Notes
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Reaction equation

HRID 1698608 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH3:30])[C:25]([OH:29])=[C:26]([Cl:28])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:28][C:26]1[CH:27]=[C:22]([Cl:21])[CH:23]=[C:24]([CH3:30])[C:25]=1[O:29][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:4]=2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 152922,4-Dichloro-6-methylphenolHCID 516892Sodium BicarbonateHCID 672728702-Chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 580123642-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazoleYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole (304 mg, 1.00 mmol), 4,6-dichloro-o-cresol (531 mg, 3.00 mmol), potassium carbonate (553 mg, 4.0 mmol) and N,N-dimethylformamide (5 ml) was heated at 110° C. for 48 h. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 10% ethyl acetate/n-hexane and recrystallization from diisopropylether/n-hexane to give 290 mg (0.65 mmol, 65%) of the title compound as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a 10% ethyl acetate/n-hexane and recrystallization from diisopropylether/n-hexane

Sources & evidence

ORD record
ord-0780ef9bca3d4be28f5a3aaa5560874e
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163935B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes