Sodium hydride → HCID 14720860, compound

HRID 36618Notes

Reaction equation

HRID 36618 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][N:20]1[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]1>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:19][N:20]3[C:24]([Cl:25])=[C:23]([Cl:26])[N:22]=[CH:21]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 146736064-(6-Chloro-2-pyridinyloxy)phenol

Product 1

HCID 14720860HCID 14720860, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

At room temperature (about 20° C.), 4.9 g of 4-(6-chloro-2-pyridinyloxy)-phenol in 40 ml of anhydrous dimethylformamide is dripped into 0.6 g of 100% strength sodium hydride in 20 ml of anhydrous dimethylformamide. The mixture is subsequently stirred for 30 minutes at 50° C, and then 4.2 g of 1-chloromethyl-4,5-dichloroimidazole in 20 ml of anhydrous dimethylformamide is dripped in at room temperature. This mixture is stirred for 2 hours at 60° C. and overnight at room temperature. It is then stirred into 200 ml of ice water and the solution is extracted three times with methyl tert-butyl ether. The organic phase is washed with 5% strength sodium hydroxide solution and water, and dried, and the solvent is evaporated off under reduced pressure. The crude product obtained is recrystallized from toluene. There is obtained 6.6 g of 1-[4-(6-chloro-2-pyridinyloxy)-phenoxymethyl]-4,5-dichloroimidazole: m.p.: 94°-98° C.

Workup

  1. customAt room temperature
  2. customis dripped in at room temperature
  3. stirringThis mixture is stirred for 2 hours at 60° C. and overnight at room temperature
  4. extractionthe solution is extracted three times with methyl tert-butyl ether
  5. washThe organic phase is washed with 5% strength sodium hydroxide solution and water
  6. customdried
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe crude product obtained
  9. customis recrystallized from toluene

Sources & evidence

ORD record
ord-d32386d5b1104b7c88d677d92e2a3a7a
Source dataset
uspto-grants-1995_05
Patent number
US05416100

Reaction notes

Loading…