Tetrahydrofuran → HCID 679919, compound

HRID 1471214Notes

Reaction equation

HRID 1471214 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

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 60 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. temperaturethe mixture was heated to 60 C for 72 hours
  2. temperatureAfter cooling to 22 C
  3. customthe reaction was quenched with water
  4. extractionextracted with ethyl acetate
  5. customFollowing solvent removal
  6. dissolutionthe product was dissolved in 8.5 ml hot ethyl acetate
  7. addition20 ml of hexane were added
  8. temperatureAfter cooling to 5 C
  9. customthe product precipitated
  10. filtrationwas filtered
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-8f76dfd8a255437599de022c3e271993
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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