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

HRID 568396Notes

Reaction equation

HRID 568396 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 1methyl-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 chlororform: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 recrystallised 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 chlororform
  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 recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-add4bb72f17a4b3aa879ac283e3f918a
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

Loading…