Water → 5-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydrofuran-2-yl)methylbenzimidazole

HRID 74278Notes

Reaction equation

HRID 74278 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][NH:7][C:8]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:9]=1[NH2:10].Cl.[C:25](=N)(OC)[CH3:26].O>CO>[O:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[C:12]1[CH:13]=[CH:14][C:8]2[N:7]([CH2:6][CH:2]3[CH2:3][CH2:4][CH2:5][O:1]3)[C:25]([CH3:26])=[N:10][C:9]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674981632-(2-(Tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674982465-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydrofuran-2-yl)methylbenzimidazoleYield 127.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(tetrahydrofuran-2-yl)methylaminoanilin-5-yl)benzoxazole (see Working Example 95-1) (0.15 g, 0.4 mmol) in methanol (5 mL) was added methyl acetimidate hydrochloride (0.05 mg, 0.4 mmol), and this was heated to reflux for 3 hours. After the reaction solution was cooled, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (0.17 g, 79% yield) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-4dc6c4a636874245a195b8c35e73cacc
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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