Water → HCID 18437798, compound

HRID 457399Notes

Reaction equation

HRID 457399 reaction equation
[Cl:1][N:2]1[C:6]([Cl:7])=[CH:5][N:4]=[CH:3]1.[H-].[Na+].[CH3:10][O:11][CH2:12][CH2:13]Cl.O>CN(C=O)C.C(OCC)(=O)C>[CH3:10][O:11][CH:12]([C:3]1[N:2]([Cl:1])[C:6]([Cl:7])=[CH:5][N:4]=1)[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 18437850HCID 18437850, compound

Product 1

HCID 18437798HCID 18437798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1 mmol of 3,4-dichloroimidazole in anhydrous DMF (5 mL) is treated with sodium hydride (1.05 mmol) at 0° C. under nitrogen with magnetic stirring. After 30 min., 2-chloroethyl methyl ether (1 mmol) is added and the reaction mixture is warmed to 60° C. for 2 h. The reaction mixture is cooled, portioned between water and ethyl acetate. The organic layer is separated, washed with water, brine and dried over sodium sulfate. The reaction mixture is filtered, evaporated and purified by chromatography on silica gel to obtain 1-methoxyethyl-3,4-dichloroimidazole.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe organic layer is separated
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe reaction mixture is filtered
  6. customevaporated
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-949e67d40e7f4bac8c1bcde4877a1c70
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

Loading…