1-Methylimidazole → HCID 86626126, compound

HRID 656714Notes

Reaction equation

HRID 656714 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[CH3:7][O:8][CH2:9][Cl:10]>ClC=C(Cl)Cl>[Cl-:10].[CH3:7][O:8][CH2:9][N:4]1[CH:5]=[CH:6][N+:2]([CH3:1])=[CH:3]1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 7864Chloromethyl Methyl Ether

Product 1

HCID 86626126HCID 86626126, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent

Procedure

Into a 500 mL round-bottomed flask equipped with a stir bar, Argon inlet and addition funnel was dissolved 1-methylimidazole (25 g, 0.31 mol) in trichloroethylene (100 mL). With stirring chloromethyl methyl ether (35 g, 0.43 mol) was added slowly dropwise over a 0.5 h period. The mixture warmed and a turbid, two-layer mixture formed upon addition. The mixture was refluxed 2 h, cooled and poured into a separatory funnel. The organic layer was separated, filtered and the solvent was removed under vacuum at 45° C. to yield a tan-beige viscous liquid (52 g).

Workup

  1. customInto a 500 mL round-bottomed flask equipped with a stir bar, Argon inlet and addition funnel
  2. temperatureThe mixture warmed
  3. customa turbid, two-layer mixture formed upon addition
  4. temperatureThe mixture was refluxed 2 h
  5. temperaturecooled
  6. additionpoured into a separatory funnel
  7. customThe organic layer was separated
  8. filtrationfiltered
  9. customthe solvent was removed under vacuum at 45° C.

Sources & evidence

ORD record
ord-1e9de483543443f88b05d56c8a8249f5
Source dataset
uspto-grants-2011_12
Patent number
US08071813B2

Reaction notes

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