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

HRID 74258Notes

Reaction equation

HRID 74258 reaction equation
[CH2:1]([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])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.[C:24](=N)(OC)[CH3:25].C(=O)([O-])O.[Na+]>CO>[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]([CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[C:24]([CH3:25])=[N:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674978662-(2-Neopentylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674980415-(Benzoxazol-2-yl)-2-methyl-1-neopentylbenzimidazoleYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-neopentylaminoanilin-5-yl)benzoxazole (see Working Example 81-2) (192 mg, 0.650 mmol) was added methyl acetimidate hydrochloride (107 mg, 0.975 mmol), and this was heated to reflux for 2 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with ethyl acetate. 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 (155 mg, 75% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. extractionthis was extracted with ethyl acetate
  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-6afd0dc9d4274c34b7cb3c215efa26de
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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