Acetic Acid → 5-(Benzoxazol-2-yl)-1-(3-methoxycarbonylphenylmethyl)-2-methylbenzimidazole

HRID 74302Notes

Reaction equation

HRID 74302 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][C:14]=2[N+:28]([O-])=O)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:31](O)(=O)[CH3:32]>[Fe]>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH2:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[C:31]([CH3:32])=[N:28][C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 674974692-(2-(3-Methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole

Product 1

HCID 674984625-(Benzoxazol-2-yl)-1-(3-methoxycarbonylphenylmethyl)-2-methylbenzimidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To 2-(2-(3-methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole (see Working Example 117-1) (220 mg, 0.545 mmol) was added iron powder (91.4 mg, 1.64 mmol) and acetic acid (5 mL), and this was heated to reflux for 12 hours. After the reaction solution was cooled, it was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (139 mg, 64% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 12 hours
  3. temperatureAfter the reaction solution was cooled
  4. concentrationit was concentrated
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc2478c7f9bd4023bb5d99c363697c9d
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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