Ethyl Acetate → HCID 14720869, compound

HRID 257756Notes

Reaction equation

HRID 257756 reaction equation
[CH3:1][C:2]1[C:3]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.[H-].[Na+].Cl[CH2:20][N:21]1[C:25]([Cl:26])=[C:24]([Cl:27])[N:23]=[CH:22]1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][C:2]1[C:3]([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:20][N:21]3[C:25]([Cl:26])=[C:24]([Cl:27])[N:23]=[CH:22]3)=[CH:12][CH:11]=2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 199376084-[(3,6-Dimethyl-2-pyrazinyl)oxy]phenol

Product 1

HCID 14720869HCID 14720869, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

At room temperature (about 20° C.), 7.8 g of 4-(3,6-dimethyl-2-pyrazinyloxy)-phenol in 20 ml of anhydrous dimethylformamide is dripped into 1.3 g of 80% strength sodium hydride in 30 ml of anhydrous dimethylformamide. The mixture is stirred for one hour at 70° C., and then 6.68 g of 1-chloromethyl-4,5-dichloroimidazole in 30 ml of anhydrous dimethylformamide is dripped in. The mixture is stirred for 8 hours at 70° C. and overnight at room temperature. It is then stirred into 200 ml of ethyl acetate, and this mixture is washed twice with water, four times with 5% strength sodium hydroxide solution and twice with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and the solvent is evaporated off under reduced pressure. The crude product obtained is crystallized with n-hexane. There is obtained 8.9 g of 1-[4-(3,6-dimethyl-2-pyrazinyloxy)-phenoxymethyl]-4,5-dichloroimidazole; m.p.: 84°-85° C.

Workup

  1. customAt room temperature
  2. stirringThe mixture is stirred for 8 hours at 70° C. and overnight at room temperature
  3. washthis mixture is washed twice with water, four times with 5% strength sodium hydroxide solution and twice with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe crude product obtained
  7. customis crystallized with n-hexane

Sources & evidence

ORD record
ord-c3ef473da2ed47b7964c1bc0f961abc9
Source dataset
uspto-grants-1993_11
Patent number
US05264434

Reaction notes

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