Sodium Bicarbonate → Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate

HRID 1698578Notes

Reaction equation

HRID 1698578 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=[C:11]([Cl:12])[C:4]=2[N:3]=1.[Cl:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:21]([NH2:22])=[C:20]([O:26][CH3:27])[CH:19]=1.C(=O)([O-])O.[Na+]>>[Cl:12][C:11]1[C:4]2[N:3]=[C:2]([NH:22][C:21]3[C:23]([CH3:25])=[CH:24][C:18]([Cl:17])=[CH:19][C:20]=3[O:26][CH3:27])[N:6]([CH3:7])[C:5]=2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 67272934Methyl 2,4-dichloro-1-methyl-1H-benzimidazole-7-carboxylate

Product 1

HCID 67273388Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylateYield 44%

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 2,4-dichloro-1-methyl-1H-benzimidazole-7-carboxylate (100 mg, 0.39 mmol) and 4-chloro-2-methoxy-6-methylaniline (200 mg, 1.17 mmol) was stirred at 130° C. overnight. After cooling, the reaction mixture was neutralized by aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on a silica gel column to give 68 mg (0.17 mmol, 44%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organics was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-9294182378cd4f4c875260c7e9d0e64f
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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