Sodium Bicarbonate → 5-(Benzoxazol-2-yl)-2-methyl-1-(2-picolyl)benzimidazole

HRID 74252Notes

Reaction equation

HRID 74252 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][C:10]=1[NH2:11].Cl.[C:26](=N)(OC)[CH3:27].C(=O)([O-])O.[Na+]>CO>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:13]1[CH:14]=[CH:15][C:9]2[N:8]([CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:26]([CH3:27])=[N:11][C:10]=2[CH:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674984162-(2-(2-Picolyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674991885-(Benzoxazol-2-yl)-2-methyl-1-(2-picolyl)benzimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-(2-picolyl)aminoanilin-5-yl)benzoxazole (see Working Example 79-1) (250 mg, 0.79 mmol) was added methyl acetimidate hydrochloride (100 mg, 0.87 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (250 mg, 93% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. extractionthis was extracted with chloroform
  4. customThe organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationafter which it was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a1ef495c74f642e1896c6d90d5112392
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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