Acetic Acid → N2-(4-Bromo-2-methoxy-6-methylphenyl)-N7,N7-bis(2-methoxyethyl)-1-methyl-1H-benzimidazole-2,7-diamine

HRID 2235552Notes

Reaction equation

HRID 2235552 reaction equation
COC(OC)[CH2:4][CH2:5][O:6][CH3:7].[Br:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][C:19]2[N:23]([CH3:24])[C:22]3[C:25]([NH2:29])=[CH:26][CH:27]=[CH:28][C:21]=3[N:20]=2)=[C:13]([O:30][CH3:31])[CH:12]=1.[C:32]([OH:35])(=O)[CH3:33].[CH:36](Cl)(Cl)Cl>CO.[Fe](Cl)Cl>[Br:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][C:19]2[N:23]([CH3:24])[C:22]3[C:25]([N:29]([CH2:4][CH2:5][O:6][CH3:7])[CH2:33][CH2:32][O:35][CH3:36])=[CH:26][CH:27]=[CH:28][C:21]=3[N:20]=2)=[C:13]([O:30][CH3:31])[CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 843481,1,3-TrimethoxypropaneHCID 86761105N2-(4-bromo-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazole-2,7-diamine

Product 1

HCID 11271502N2-(4-Bromo-2-methoxy-6-methylphenyl)-N7,N7-bis(2-methoxyethyl)-1-methyl-1H-benzimidazole-2,7-diamineYield 18%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 200 mg (1.66 mmol) of 1,1,3-trimethoxypropane in 25 mL of chloroform was added 5 g (1.66 mmol) of iron (II) chloride on silica (5% by weight) and the slurry was stirred at room temperature for several hours. The slurry was filtered, concentrated in vacuo to about 5 mL and added to a slurry of 200 mg (0.55 mmol) of N2-(4-bromo-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazole-2,7-diamine, 1 mL of acetic acid and 2.5 g (5.08 mmol) of MP-CNBH3 in 10 mL of methanol and was stirred overnight. The above aldehyde preparation was repeated each day for 7 days and added to the reaction. The reaction was filtered and concentrated in vacuo to a residue. The residue was purified by flash chromatography eluting with a solution of 40% ethyl acetate/hexanes containing 2% ammonium hydroxide to give 47 mg (18%) of the title compound.

Workup

  1. filtrationThe slurry was filtered
  2. concentrationconcentrated in vacuo to about 5 mL
  3. stirringwas stirred overnight
  4. additionadded to the reaction
  5. filtrationThe reaction was filtered
  6. concentrationconcentrated in vacuo to a residue
  7. customThe residue was purified by flash chromatography
  8. washeluting with a solution of 40% ethyl acetate/hexanes containing 2% ammonium hydroxide

Sources & evidence

ORD record
ord-b06d0a4df3924d5c9d5d230cef59a1a0
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

Loading…