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

HRID 74255Notes

Reaction equation

HRID 74255 reaction equation
[CH:1]([NH:4][C:5]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:6]=1[NH2:7])([CH3:3])[CH3:2].Cl.[C:22](=N)(OC)[CH3:23].C(=O)([O-])O.[Na+]>CO>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:5]2[N:4]([CH:1]([CH3:3])[CH3:2])[C:22]([CH3:23])=[N:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674987282-(2-Isopropylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674984945-(Benzoxazol-2-yl)-2-methyl-1-isopropylbenzimidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-isopropylaminoanilin-5-yl)benzoxazole (see Working Example 80-2) (180 mg, 0.673 mmol) was added methyl acetimidate hydrochloride (111 mg, 1.01 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 (196 mg, quant.) 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-ef18bb436d9f4655a96ff12b1d9b6132
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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