N-methyl-2-pyrrolidone → 1-(4-Amino-3-cyano-5-methylphenyl)-2,4-dimethylimidazole

HRID 2231662Notes

Reaction equation

HRID 2231662 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]2[CH3:15])=[CH:4][C:3]=1Br.[CH3:17][N:18]1CCCC1=O>>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]2[CH3:15])=[CH:4][C:3]=1[C:17]#[N:18]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 144502861-(4-Amino-3-bromo-5-methylphenyl)-2,4-dimethylimidazole

Product 1

HCID 144502881-(4-Amino-3-cyano-5-methylphenyl)-2,4-dimethylimidazole

Procedure

A mixture of 1-(4-amino-3-bromo-5-methylphenyl)-2,4-dimethylimidazole (17.3 g) and cuprous cyanide (17.9 g) was heated and stirred at 150° in N-methylpyrrolidone (50 cm3) for 6 hours. The cooled mixture was partitioned between ammonia solution (200 cm3 ; S.G. 0.880) and chloroform (200 cm3). The aqueous phase was extracted further with chloroform (2×100 cm3), and the combined and dried (MgSO4) organic phases were evaporated in vacuo to give an oil, which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]), eluting with dichloromethane:methanol, 19:1. Combination and evaporation of the appropriate fractions gave an oil which was triturated with ether to give a solid (10.05 g). A small portion of this material was recrystallised from ethyl acetate-methanol to afford the title compound, m.p. 214°-217°.

Workup

  1. temperaturewas heated
  2. customThe cooled mixture was partitioned between ammonia solution (200 cm3 ; S.G. 0.880) and chloroform (200 cm3)
  3. extractionThe aqueous phase was extracted further with chloroform (2×100 cm3)
  4. dry with materialdried (MgSO4) organic phases
  5. customwere evaporated in vacuo
  6. customto give an oil, which
  7. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with dichloromethane
  9. customCombination and evaporation of the appropriate fractions
  10. customgave an oil which
  11. customwas triturated with ether

Sources & evidence

ORD record
ord-05ef2964ec904945b6cddc54fa7db8be
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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