Tetrahydrofuran → HCID 20432649, compound

HRID 2412436Notes

Reaction equation

HRID 2412436 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([C:13](=O)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH2:21])([CH3:3])[CH3:2].O1CCC[CH2:23]1.C[Mg]Br.C(OCC)(=O)C>C(OCC)C>[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH2:23])[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH2:21])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 20432643HCID 20432643, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 20432649HCID 20432649, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Three grams (10.7 mmoles) of 1-isopropyl-2-amino-6-benzoylbenzimidazole were dissolved in 25 ml. of tetrahydrofuran, after which was added 27 ml. of a 2M solution of methyl magnesium bromide in ethyl ether. After stirring overnight, ethyl acetate was added, and the solution was washed three times with a saturated sodium chloride solution. The organic solution was dried over magnesium sulfate, filtered, and evaporated under reduced pressure. One hundred milliliters of 98% formic acid were added to the residue. The solution was refluxed for 2 hours. The formic acid was evaporated under reduced pressure. Ethyl acetate was added, and the resulting solution was washed with a saturated sodium bicarbonate solution. After drying over magnesium sulfate, the solution was filtered and concentrated. Upon the addition of a small volume of ether, 2.0 g. of the title product solidified out of solution which was recovered by filtration, M+ =277.

Workup

  1. washthe solution was washed three times with a saturated sodium chloride solution
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. additionOne hundred milliliters of 98% formic acid were added to the residue
  6. temperatureThe solution was refluxed for 2 hours
  7. customThe formic acid was evaporated under reduced pressure
  8. additionEthyl acetate was added
  9. washthe resulting solution was washed with a saturated sodium bicarbonate solution
  10. dry with materialAfter drying over magnesium sulfate
  11. filtrationthe solution was filtered
  12. concentrationconcentrated
  13. additionUpon the addition of a small volume of ether, 2.0 g
  14. filtrationwas recovered by filtration, M+ =277

Sources & evidence

ORD record
ord-2a68ebc8e2dc4f7c82bcee4544f73740
Source dataset
uspto-grants-1985_01
Patent number
US04492708

Reaction notes

Loading…