Sodium hydride → HCID 19006056, compound

HRID 248909Notes

Reaction equation

HRID 248909 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[H-].[Na+].[H][H].Cl[CH2:19][N:20]1[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]1>CN(C)C=O>[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:19][N:20]2[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 24744926HCID 24744926, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19006056HCID 19006056, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

Under a nitrogen blanket and at room temperature, 5.8 g of 4-(3,3-dimethyl-1-proplyoxy)-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 hydrogen evolution has subsided, the mixture is stirred for a further hour 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 then stirred for 3 hours at 80° C. and overnight at room temperature. The mixture is then poured into 100 ml of ice water, followed by extraction three times with methyl tert-butyl ether. The organic phases are washed with 5% strength sodium hydroxide solution and three times with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from cyclohexane. There is obtained 7.4 g of 1-[4-(3,3-dimethyl-1-propyloxy)-phenoxymethyl]-4,5-dichloroimidazole having a melting point of 105°-108° C.

Workup

  1. customat room temperature
  2. customis dripped in at room temperature
  3. stirringThe whole is then stirred for 3 hours at 80° C. and overnight at room temperature
  4. extractionfollowed by extraction three times with methyl tert-butyl ether
  5. washThe organic phases are washed with 5% strength sodium hydroxide solution and three times with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-e368ff45fc2541ecb9571cb13872abf4
Source dataset
uspto-grants-1993_05
Patent number
US05212194

Reaction notes

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