Potassium Carbonate → HCID 22130262, compound

HRID 1416003Notes

Reaction equation

HRID 1416003 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][F:35]>CS(C)=O.O>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:34][F:35])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

Product 1

HCID 22130262HCID 22130262, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
1.5 °C

Procedure

In dimethylsulfoxide (20 ml)was dissolved 814 mg (2.0 mmol)of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropylimidazole (16a), with cooling to 0 to 3° C., followed by addition of 1.44 g (10.4 mmol)of potassium carbonate with stirring, and the mixture was stirred at the same temperature for 15 minutes. Then, 270 mg (2.40 mmol)of bromofluoromethane was added, and the mixture was stirred for 30 minutes at the same temperature and then for 3 hours at room temperature, and left overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, and the organic layer was washed with water and dried over sodium sulfate. The solvent was concentrated under reduced pressure, and the crude product was fractionated by silica gel column chromatography (ethyl acetate:methylene chloride=1:19). From the first fraction, 137 mg (yield 16%)of positional isomer (17x')of the target compound was obtained as oil. From the subsequent fraction, 700 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-fluoromethyl-4-isopropyl-1H-imidazole (17x)of the target compound was obtained as oil (yield 80%).

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 minutes
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. waitleft overnight
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customFrom the first fraction, 137 mg (yield 16%)of positional isomer (17x')of the target compound was obtained as oil

Sources & evidence

ORD record
ord-de30580a9ab647358614524b17cda7c3
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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