Sodium Bicarbonate → HCID 58012362, compound

HRID 1698545Notes

Reaction equation

HRID 1698545 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19])=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:20][C:21]1[CH:27]=[C:26]([CH3:28])[C:24]([NH2:25])=[C:23]([O:29][CH3:30])[CH:22]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Br:20][C:21]1[CH:27]=[C:26]([CH3:28])[C:24]([NH:25][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH2:18][CH3:19])=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:23]([O:29][CH3:30])[CH:22]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 106802184-Bromo-2-methoxy-6-methylanilineHCID 67273043HCID 67273043, compound

Product 1

HCID 58012362HCID 58012362, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 100 mg (0.369 mmol) of 2-chloro-7-(2-ethylphenyl)-1-methyl-1H-benzimidazole and 239 mg (1.11 mmol) of 4-bromo-2-methoxy-6-methylaniline was stirred at 120° C. for 15 hours. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate, followed by addition of ethyl acetate. The resulting crystals were collected by filtration and washed with water and ethyl acetate, and suspended in hot ethyl acetate. After cooling to room temperature, the crystals were collected by filtration and washed with ethyl acetate and a 50% dimethylsulfoxide/methanol mixture to give 90 mg (54%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water and ethyl acetate
  4. temperatureAfter cooling to room temperature
  5. filtrationthe crystals were collected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-28918a6c8bc64e0488f7d7a2fd6b6f38
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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