Bis(2-chloroethyl) ether → HCID 12832386, compound

HRID 370772Notes

Reaction equation

HRID 370772 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1.ClC[CH2:26][O:27][CH2:28]CCl>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]2[N:14]=[CH:13][N:12]([CH2:26][O:27][CH3:28])[C:11]=2[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 14100143HCID 14100143, compound

Product 1

HCID 12832386HCID 12832386, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

Incremental portions of 3.6 g of sodium hydride (50% strength in white oil) is added to a solution of 21 g of 4,5-bis(4-methoxyphenyl)imidazole in 75 ml of absolute dimethylformamide. The mixture is stirred for another 30 minutes, and then 6.3 ml of 1-chloromethylmethyl ether in 35 ml of dimethylformamide is added dropwise. After 30 minutes the mixture is poured on ice water, the product is taken up in chloroform, the organic solution is washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is crystallized from benzene/hexane, thus obtaining 18.31 g of 4,5-bis(4-methoxyphenyl)-1-methoxymethylimidazole, mp 99°-101°.

Workup

  1. additionAfter 30 minutes the mixture is poured on ice water
  2. washthe organic solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is crystallized from benzene/hexane

Sources & evidence

ORD record
ord-7b663021568c4a5fa0629ec869db3bc1
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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