Water → HCID 54388388, compound

HRID 343291Notes

Reaction equation

HRID 343291 reaction equation
[Cl:1][C:2]1[NH:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[CH:16](I)([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.C(OCC)C>[Cl:1][C:2]1[N:6]([CH:16]([CH3:18])[CH3:17])[C:5]([CH3:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 54002462HCID 54002462, compound

Product 1

HCID 54388388HCID 54388388, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8.9 grams (0.04 mole) of 5-chloro-4-(4-methoxyphenyl)-2-methyl-imidazole, 34.0 grams (0.20 mole) of isopropyl iodide, and 27.8 grams (0.02 mole) of potassium carbonate in 200 mL of acetone is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is shaken with 100 mL of water and 100 mL of diethyl ether. The organic layer is separated, washed with water, and dried with magnesium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure to a residue. The residue is purified with column chromatography, yielding 5-chloro-1-(1-methylethyl)-4-(4-methoxyphenyl)-2-methylimidazole.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialdried with magnesium sulfate
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure to a residue
  6. customThe residue is purified with column chromatography

Sources & evidence

ORD record
ord-4fc78d513c6445ab81b27f5f4fade7d8
Source dataset
uspto-grants-1999_01
Patent number
US05861359

Reaction notes

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