Tetrahydrofuran → HCID 679919, compound

HRID 1926467Notes

Reaction equation

HRID 1926467 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1)[CH3:2].[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].O1[CH2:21][CH2:20]CC1>>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:4]1[N:3]([CH2:1][CH3:2])[C:14]2[CH:13]=[CH:12][CH:20]=[CH:21][C:15]=2[N:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4850941-Ethyl-1H-benzimidazoleHCID 178418339Butyllithium

Product 1

HCID 679919HCID 679919, compound

Conditions

Temperature
6 °C

Procedure

To a flask were added 2.0 g 1-ethyl-1H-benzimidazole and 25 ml tetrahydrofuran under nitrogen. To this solution was added 20 ml n-butyllitium (1.6M) and the mixture was heated to 6° C. for 72 hours. After cooling to 22 C, the reaction was quenched with water and extracted with ethyl acetate. Following solvent removal, the product was dissolved in 8.5 ml hot ethyl acetate and 20 ml of hexane were added. After cooling to 5 C, the product precipitated and was filtered, washed with hexane, and dried giving 0.42 g pale yellow solid.

Workup

  1. temperatureAfter cooling to 22 C
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customFollowing solvent removal
  5. dissolutionthe product was dissolved in 8.5 ml hot ethyl acetate
  6. addition20 ml of hexane were added
  7. temperatureAfter cooling to 5 C
  8. customthe product precipitated
  9. filtrationwas filtered
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-e4dc0638e76f4a1f8ba00829df3ba589
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

Loading…