Methanol → 5-(Benzoxazol-2-yl)-1-(2-hydroxyethyl)-2-methylbenzimidazole

HRID 74270Notes

Reaction equation

HRID 74270 reaction equation
CO.[OH:3][CH2:4][CH2:5][NH:6][C:7]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][C:8]=1[NH2:9].Cl.[C:24](=N)(OC)[CH3:25]>O>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:11]1[CH:12]=[CH:13][C:7]2[N:6]([CH2:5][CH2:4][OH:3])[C:24]([CH3:25])=[N:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674988842-(2-(2-Hydroxyethyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674988205-(Benzoxazol-2-yl)-1-(2-hydroxyethyl)-2-methylbenzimidazoleYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-(2-hydroxyethyl)aminoanilin-5-yl)benzoxazole (see Working Example 88-1) (0.10 g, 0.4 mmol) was added methyl acetimidate hydrochloride (0.08 g, 0.7 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (0.05 g, 49% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe precipitated crystals were filtered
  4. washafter being washed with water
  5. customwere dried

Sources & evidence

ORD record
ord-4d905d6b96b34371953861aa49e991ae
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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