Hydrochloric Acid → 3-Methyl-4-((1-methyl-1H-benzimidazol-5-yl)oxy)benzenamine

HRID 240560Notes

Reaction equation

HRID 240560 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:20]C=O)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:19]=[CH:18][C:13]2[N:14]([CH3:17])[CH:15]=[N:16][C:12]=2[CH:11]=1.C(=O)(O)[O-].[Na+]>CO.O>[CH3:2][C:3]1[CH:4]=[C:5]([NH2:20])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:19]=[CH:18][C:13]2[N:14]([CH3:17])[CH:15]=[N:16][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86650897N-(3-methyl-4-(1-methyl-1H-benzo[d]imidazol-5-yloxy)phenyl)formamide

Product 1

HCID 669369553-Methyl-4-((1-methyl-1H-benzimidazol-5-yl)oxy)benzenamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of concentrated aqueous HCl (10 mL) in methanol (10 mL) was added N-(3-methyl-4-(1-methyl-1H-benzo[d]imidazol-5-yloxy)phenyl)formamide (1.70 g, 6.04 mmol). After heating to reflux for 2 hours, the reaction mixture was cooled to room temperature and diluted with water (100 mL). The mixture was neutralized with sodium bicarbonate and extracted with dichloromethane. The organic solution was dried over Na2SO4, filtered and concentrated under reduced pressure to provide the product.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2 hours
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide the product

Sources & evidence

ORD record
ord-4439c8b887064b17aa1a606901c67f91
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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