Imidazole → HCID 12151214, compound

HRID 2415035Notes

Reaction equation

HRID 2415035 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4](S(C(C)C)(=O)=O)[N:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24].[H-].[Na+].[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1>O1CCCC1.O>[N:27]1([C:2]2[C:7]([I:8])=[C:6]([C:9]([F:10])([F:11])[F:12])[N:5]=[C:4]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[N:3]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 12151421HCID 12151421, compound

Product 1

HCID 12151214HCID 12151214, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (0.50 g) was dissolved in tetrahydrofuran (5.0 ml) and added 2-pyrrolidinone (0.10 g). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 36 mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.25 g) at the same temperature. The mixture was stirred at that temperature for 30 minutes, and then it warmed to room temperature After stirg over night, the mixture was added water and extracted with ethyl acetate. The ethyl acetate 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 1-(4-imidazol-1-yl-5-iodo-6-trifluoromethylpyrimidin-2-yl)-pyrrolidin-2-one (0.20 g) as colorless crystalline solid, mp 195-197° C.

Workup

  1. temperatureThe mixture was cooled to ice bath temperature
  2. stirringThe mixture was stirred at that temperature for 30 minutes
  3. waitAfter stirg over night
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water and brine
  6. dry with materialrespectively and dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform-THF)

Sources & evidence

ORD record
ord-5ca8e535d73645d2a94a39852b9f9c0c
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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