Imidazole → HCID 53853558, compound

HRID 581837Notes

Reaction equation

HRID 581837 reaction equation
[I:1]I.[CH3:3][O:4][C:5]([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>C1(C)C=CC=CC=1>[I:1][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:5]([O:4][CH3:3])=[O:6])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 53671163HCID 53671163, compound

Product 1

HCID 53853558HCID 53853558, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.5 g (21.6 mmol) of iodine are added to a solution of 4.16 g (19.6 mmol) of 2-(4-methoxycarbonylmethyloxyphenyl)-ethanol, 5.7 g (21.6 mmol) of triphenylphosphine and 1.84 g (29.3 mmol) of imidazole in 200 ml of toluene at room temperature, while stirring, and stirring is continued at room temperature for one hour. A precipitate separates out and is filtered off with suction and discarded. The mother liquor is concentrated to dryness under reduced pressure and the residue is heated with petroleum ether. The triphenyl oxide which has precipitated out is filtered off with suction and the mother liquor is concentrated to dryness again. A crude oil remains.

Workup

  1. stirringstirring
  2. filtrationis filtered off with suction
  3. concentrationThe mother liquor is concentrated to dryness under reduced pressure
  4. temperaturethe residue is heated with petroleum ether
  5. customThe triphenyl oxide which has precipitated out
  6. filtrationis filtered off with suction
  7. concentrationthe mother liquor is concentrated to dryness again

Sources & evidence

ORD record
ord-a9e37759e16a416faeda8131b770e44b
Source dataset
uspto-grants-1999_07
Patent number
US05922717

Reaction notes

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