Formic Acid → N-(3-methyl-4-(1-methyl-1H-benzo[d]imidazol-5-yloxy)phenyl)formamide

HRID 240559

Reaction equation

HRID 240559 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH2:15])[C:10]([NH:13][CH3:14])=[CH:11][CH:12]=2)=[C:4]([CH3:18])[CH:3]=1.O.[C:20](=[O:23])(O)[O-].[Na+].[CH:25](O)=O>>[CH3:18][C:4]1[CH:3]=[C:2]([NH:1][CH:20]=[O:23])[CH:17]=[CH:16][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]2[N:13]([CH3:25])[CH:14]=[N:15][C:9]=2[CH:8]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 669371924-(4-amino-2-methylphenoxy)-N1-methylbenzene-1,2-diamine

Product 1

HCID 86650897N-(3-methyl-4-(1-methyl-1H-benzo[d]imidazol-5-yloxy)phenyl)formamideYield 97%

Procedure

4-(4-amino-2-methylphenoxy)-N1-methylbenzene-1,2-diamine (1.52 g, 6.25 mmol) was dissolved in formic acid (15 mL) and heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted water (100 mL) and neutralized with sodium bicarbonate. The mixture was partitioned between water and dichloromethane. The organic layer was washed with aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide the product (1.70 g, 97%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. customThe mixture was partitioned between water and dichloromethane
  4. washThe organic layer was washed with aqueous NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0dab9ef9b5224f3f803afa2d4cdf7185
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Linked notes

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