1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone → HCID 10670941, compound

HRID 1489435Notes

Reaction equation

HRID 1489435 reaction equation
[F:1][C:2]([F:19])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][NH:15][C:14]2=[O:18])=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28](=[O:39])[C@@H:29](OS(C(F)(F)F)(=O)=O)[CH3:30]>CN1CCCC1=O.[H-].[Na+].O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28](=[O:39])[C@H:29]([N:15]1[CH:16]=[CH:17][N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:2]([F:1])([F:19])[CH:3]([F:4])[F:5])=[CH:8][CH:9]=2)[C:14]1=[O:18])[CH3:30]

Participants

8

Reactant 2

HCID 105643671-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazoloneHCID 10710636HCID 10710636, compound

Product 1

HCID 10670941HCID 10670941, compoundYield 41.1%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 24758Sodium hydrideSolvent

Procedure

1-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (1.42 g) was dissolved in 10 ml of 1-methyl-2-pyrrolidone, to which 60% sodium hydride in oil (0.198 g) was added. The mixture was stirred at room temperature for 30 minutes. The reaction solution was ice-cooled and added dropwise under nitrogen atmosphere over the period of 10 minutes to a solution of 1.8 g of (2S)-2', 4'-difluoro-2-trifluoromethanesulfonyloxypropiophenone in 50 ml of tetrahydrofuran which was cooled to -40° C. Then, the reaction temperature was raised to -20° C. over the period of 20 minutes and the reaction solution was stirred for 10 minutes. The reaction solution was diluted with 3.5 ml of acetic acid and 70 ml of ethyl acetate, washed with water (40 ml×2), 0.5N-hydrochloric acid (40 ml×2) and 40 ml of a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium chloride. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (silica gel: 300 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.08) to give 0.94 g of 1-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone as a pale yellow viscous substance. The product was crystallized from a mixture of diisopropyl ether and hexane to give colorless powdery crystals.

Workup

  1. additionwas added
  2. temperaturecooled
  3. temperaturewas cooled to -40° C
  4. temperatureThen, the reaction temperature was raised to -20° C. over the period of 20 minutes
  5. stirringthe reaction solution was stirred for 10 minutes
  6. washwashed with water (40 ml×2), 0.5N-hydrochloric acid (40 ml×2) and 40 ml of a saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium chloride
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel chromatography (silica gel: 300 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.08)

Sources & evidence

ORD record
ord-002df35b426c49b28eed49d57866af04
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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