Sodium hydride → 1-[4-(1-Methyl-1-propyloxy)-phenoxymethyl]-4,5-dichloroimidazole

HRID 1742829Notes

Reaction equation

HRID 1742829 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].[H-].[Na+].[H][H].Cl[CH2:18][N:19]1[C:23]([Cl:24])=[C:22]([Cl:25])[N:21]=[CH:20]1>CN(C)C=O>[CH3:1][CH:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:18][N:19]2[C:23]([Cl:24])=[C:22]([Cl:25])[N:21]=[CH:20]2)=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 138820044-(1-Methyl-1-propyloxy)-phenolHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 146768971-[4-(1-Methyl-1-propyloxy)-phenoxymethyl]-4,5-dichloroimidazoleYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

Under a nitrogen blanket and at room temperature (about 20° C.), 5.0 g of 4-(1-methyl-1-propyloxy)-phenol in 20 ml of anhydrous dimethylformamide is dripped into 0.79 g of 80% strength sodium hydride in 50 ml of anhydrous dimethylformamide. After the exothermic reaction has subsided (evolution of hydrogen), the mixture is stirred for a further 30 minutes at 60° C. Subsequently, 6.12 g of 1-chloromethyl-4,5-dichloroimidazole in 20 ml of anhydrous dimethylformamide is dripped in at room temperature. The whole is poured into 150 ml of ice water, followed by extraction three times with ethyl acetate. The organic phases are washed with 5strength sodium hydroxide solution and with water. Drying over sodium sulfate and concentration under reduced pressure gives a crude product which is purified by chromatography on silica gel using toluene/ethyl acetate (9:1) as eluant. There is obtained 4.3 g of 1-[4-(1-methyl-1-propyloxy)-phenoxymethyl]-4,5-dichloroimidazole; n22D =1.5475.

Workup

  1. customat room temperature
  2. customAfter the exothermic reaction
  3. customis dripped in at room temperature
  4. extractionfollowed by extraction three times with ethyl acetate
  5. washThe organic phases are washed with 5strength sodium hydroxide solution and with water
  6. dry with materialDrying over sodium sulfate and concentration under reduced pressure
  7. customgives a crude product which
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-93a4b10d66fe4382bbceef51587a5ce3
Source dataset
uspto-grants-1994_08
Patent number
US05342849

Reaction notes

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