1,4-Dioxane → HCID 18412392, compound

HRID 2288516Notes

Reaction equation

HRID 2288516 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:9][O:10][CH3:11])[N:6]([CH3:8])[CH:7]=1.OCC1N(C)C(COC)=NC=1.[Cl:23]N1C(=O)CCC1=O.O1CCOCC1>C(OCCO)C>[Cl:23][C:7]1[N:6]([CH3:8])[C:5]([CH2:9][O:10][CH3:11])=[N:4][C:3]=1[CH2:2][OH:1]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 31398ChlorosuccinimideHCID 18412327HCID 18412327, compoundHCID 184125074-Hydroxymethyl-2-methoxymethyl-1-methyl-imidazole

Product 1

HCID 18412392HCID 18412392, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A 1:1 mixture of 7.7 g (49 mmol) of 4-hydroxymethyl-2-methoxymethyl-1-methyl-imidazole and 5-hydroxymethyl-2-methoxymethyl-1-methyl-imidazole and 7.3 g (55 mmol) of N-chloro-succinimide was heated to 50° C. in 48 ml of ethylene glycol monoethylether and 70 ml of dioxan for 10 hours. Then the solvent was distilled off in vacuo and the crude product purified by chromatography (silica gel; methylene chloride/ethanol=99:1 to 90:10) to obtain the isomerically pure title compound. Yield: 3.4 g (36% of theory), Rf value: 0.40 (silica gel; methylene chloride/ethanol=19:1)

Workup

  1. distillationThen the solvent was distilled off in vacuo
  2. customthe crude product purified by chromatography (silica gel; methylene chloride/ethanol=99:1 to 90:10)

Sources & evidence

ORD record
ord-3770f4a82e524777b91fb5ee85741996
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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