Sodium Bicarbonate → 5-(Benzoxazol-2-yl)-1-n-butyl-2-methylbenzimidazole

HRID 74246Notes

Reaction equation

HRID 74246 reaction equation
[CH2:1]([NH:5][C:6]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:7]=1[NH2:8])[CH2:2][CH2:3][CH3:4].Cl.[C:23](=N)(OC)[CH3:24].C(=O)([O-])O.[Na+]>CO>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:6]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:23]([CH3:24])=[N:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674988512-(2-n-Butylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674980295-(Benzoxazol-2-yl)-1-n-butyl-2-methylbenzimidazoleYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-n-butylaminoanilin-5-yl)benzoxazole (see Working Example 74-2) (300 mg, 1.07 mmol) was added methyl acetimidate hydrochloride (175 mg, 1.60 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. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were purified by silica gel column chromatography to yield the title compound (293 mg, 90% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. extractionthis was extracted with chloroform
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crystals obtained
  9. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-05e87679402e4f8594f18771b0703655
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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