Dimethylformamide → HCID 15869809, compound

HRID 1739377Notes

Reaction equation

HRID 1739377 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH:10]([C:12]2[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=2)[OH:11])=[C:4]([CH3:24])[CH:3]=1.CN(C)C=O.[CH2:30](Br)[CH3:31].[H-].[Na+]>CCOCC>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH:10]([C:12]2[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=2)[O:11][CH2:30][CH3:31])=[C:4]([CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 15869808HCID 15869808, compound

Product 1

HCID 15869809HCID 15869809, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 0.34 g (0.9 mmol) of 2-[2-(4-chloro-2-methylphenoxymethyl)-α-hydroxybenzyl]-1-methylimidazole, 3 ml of N,N-dimethylformamide and 0.13 ml (1.8 mmol) of ethyl bromide was added 0.05 g (1.3 mmol) of 60% sodium hydride under ice-cooling and stirred at the same temperature for 3 hours. After completion of the reaction, 100 ml of ether was added and washed twice with 80 ml of brine. The ether layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-[2-(4-chloro-2-methylphenoxymethyl)-α-ethoxybenzyl]-1-methylimidazole (0.30 g, 89.9%) as colorless oil.

Workup

  1. temperaturecooling
  2. additionwas added
  3. washwashed twice with 80 ml of brine
  4. dry with materialThe ether layer was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-28f3b66c079f4361b8f564301545937a
Source dataset
uspto-grants-1999_10
Patent number
US05965740

Reaction notes

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