Imidazole → HCID 12151218, compound

HRID 2415037Notes

Reaction equation

HRID 2415037 reaction equation
Cl[C:2]1[C:7]([C:8]([Cl:10])=[CH2:9])=[C:6]([C:11]([F:14])([F:13])[F:12])[N:5]=[C:4]([CH3:15])[N:3]=1.[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.O>C(#N)C>[Cl:10][C:8]([C:7]1[C:2]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[N:3][C:4]([CH3:15])=[N:5][C:6]=1[C:11]([F:14])([F:13])[F:12])=[CH2:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 12151217HCID 12151217, compound

Product 1

HCID 12151218HCID 12151218, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-5-(1-chlorovinyl)-2-methyl-6-trifluoromethylpyrimidine (1.83 g) was dissolved in acetonitrile (20 ml) under stirring in room temperature. The mixture was added imidazole (1.45 g) and refluxed 3 hr and then cooled to room temperature and added water. The mixture was extracted with chloroform. The chloroform layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF) to give 5-(1-chlorovinyl)-4-imidazol-1-yl-2-methyl-6-trifluoromethyl-pyrimidine (1.34 g) as pale brown oil. 1H-NMR (δ, ppm); 2.82 (s, 3H), 5.78 (d, 1H), 6.03 (d, 1H), 7.21 (br, 1H), 7.87 (br, 1H), 8.55 (br, 1H).

Workup

  1. temperaturerefluxed 3 hr
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with chloroform
  4. washThe chloroform layer was washed with water and brine
  5. dry with materialrespectively and dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform-THF)

Sources & evidence

ORD record
ord-40defeaa89da4c0d9812cb0c79f3cd46
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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