2,4,5-Trichloro-1H-imidazole → 2,4,5-Trichloro-1-[(4-chlorobutoxy)methyl]-1h-imidazole

HRID 1789341Notes

Reaction equation

HRID 1789341 reaction equation
[Na].[Cl:2][C:3]1[NH:4][C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1.[H-].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18]Cl>CN(C)C=O.O>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][N:4]1[C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=[C:3]1[Cl:2]

Participants

7

Reactant 4

HCID 243572,4,5-Trichloro-1H-imidazoleHCID 24758Sodium hydrideHCID 3146301-Chloro-4-(chloromethoxy)butaneHCID 5360545Sodium

Product 1

HCID 1841622,4,5-Trichloro-1-[(4-chlorobutoxy)methyl]-1h-imidazoleYield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of a sodium salt, prepared from 0.69 g of 2,4,5-trichloroimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 0.63 g of 4-chlorobutoxymethyl chloride at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the reaction mixture which was then extracted with three 30-ml portions of ether. The ether layer was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel to obtain 0.83 g of 1-(4-chlorobutoxymethyl)-2,4,5-trichloroimidazole.

Workup

  1. extractionwas then extracted with three 30-ml portions of ether
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe oily product obtained
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c4cc47b5c6174bd9a055b86afe362b76
Source dataset
uspto-grants-1987_08
Patent number
US04689340

Reaction notes

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