Diethyl Ether → HCID 20141783, compound

HRID 649543Notes

Reaction equation

HRID 649543 reaction equation
[CH3:1][Li].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](C#N)=[C:13](C)[N:12]=[C:11]2[CH3:18])=[CH:6][C:5]=1[CH3:19].CC[O:22][CH2:23][CH3:24]>>[C:23]([C:24]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[C:5]([CH3:19])[CH:6]=2)[C:11]([CH3:18])=[N:12][C:13]=1[CH3:14])(=[O:22])[CH3:1]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 20141786HCID 20141786, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20141783HCID 20141783, compound

Procedure

Methyllithium (219 cm3 of a 1.5M solution in ether) was added dropwise to a stirred suspension of 1-(4-amino-3-methylphenyl)-5-cyano-2,4-dimethylimidazole (9.3 g) in ether (100 cm3) at -70° under nitrogen. The mixture was allowed to warm to room temperature over 1 hour and then heated under reflux for 5 hours. The mixture was quenched by the dropwise addition of water (50 cm3), acidified with 2M hydrochloric acid (50 cm3), and warmed on a steam bath for 5 minutes. The mixture was basified with 10% sodium carbonate solution to pH9 and extracted with dichloromethane (3×200 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution of the column with hexane:ethyl acetate, 1:1, gave firstly fractions containing recovered starting material (2.9 g). Further elution with hexane:ethyl acetate, 1:4, followed by combination and evaporation of the appropriate fractions, afforded the title compound as an oil (5.6 g), which was used (Preparation 11) without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was quenched by the dropwise addition of water (50 cm3)
  4. temperaturewarmed on a steam bath for 5 minutes
  5. extractionextracted with dichloromethane (3×200 cm3)
  6. dry with materialdried (MgSO4) organic extracts
  7. customwere evaporated in vacuo
  8. customto give a residue which
  9. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  10. washElution of the column with hexane
  11. customethyl acetate, 1:1, gave firstly fractions
  12. additioncontaining
  13. customrecovered
  14. washFurther elution with hexane
  15. customethyl acetate, 1:4, followed by combination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-2a9fe77282e1430fab805ffc9d092060
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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