N-methyl-2-pyrrolidone → HCID 14450289, compound

HRID 1199541Notes

Reaction equation

HRID 1199541 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]2[CH3:18])=[CH:4][C:3]=1Br.[CH3:20][N:21]1CCCC1=O>>[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]2[CH3:18])=[CH:4][C:3]=1[C:20]#[N:21]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 14450287HCID 14450287, compound

Product 1

HCID 14450289HCID 14450289, compound

Procedure

To a stirred solution of 1-(4-amino-3-bromo-5-trifluoromethylphenyl)-2,4-dimethylimidazole (4.61 g) in 1-methyl-2-pyrrolidone (50 cm3) was added cuprous cyanide (3.7 g) and the mixture was heated at 150° for 2 days. The mixture was then cooled and the solvent evaporated in vacuo. A solution of ammonia in water (100 cm3, s.g. 0.88) was added and the aqueous phase was extracted with chloroform:methanol, 20:1 (3×100 cm3). The combined organic extracts were dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform:methanol, 50:1. Combination and evaporation of appropriate fractions gave a solid which was recrystallized from methanol/ethyl acetate to give microcrystals of 1-(4-amino-3-cyano-5-trifluoromethylphenyl)-2,4-dimethylimidazole, (1.1 g), m.p. 208°-10°.

Workup

  1. temperaturethe mixture was heated at 150° for 2 days
  2. temperatureThe mixture was then cooled
  3. customthe solvent evaporated in vacuo
  4. additionA solution of ammonia in water (100 cm3, s.g. 0.88) was added
  5. extractionthe aqueous phase was extracted with chloroform
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  10. washeluting with chloroform
  11. customCombination and evaporation of appropriate fractions
  12. customgave a solid which
  13. customwas recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-68b34613d0454483b98f5eae1973d310
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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