Ethyl Acetate → HCID 178477984, compound

HRID 1386956Notes

Reaction equation

HRID 1386956 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]([I:15])=[C:12](I)[N:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].S([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C(O)C.O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][CH:12]=[C:11]([I:15])[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 21180254HCID 21180254, compound

Product 1

HCID 178477984HCID 178477984, compoundYield 84.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-4,5-diiodo-lH-imidazole (0.93 g, 2.0 mmol) and sodium sulfite (1.01 g, 8.0 mmol) in ethanol (33 ml) and water (8 ml) was refluxed for 24 h. After addition of EtOAc (200 ml) and brine (20 ml) the organic layer was separated, then dried with Na2SO4, evaporated and chromatographed over SiO2 with EtOAc-hexane (6:1) to obtain 2-(3,4-dichloro-phenyl)-4-iodo-1H-imidazole (0.57 g, 84%) as a solid mass. Mp. 206-207° C. (EtOAc/hexane), MS: m/e=338 (M+).

Workup

  1. temperaturewas refluxed for 24 h
  2. customwas separated
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customchromatographed over SiO2 with EtOAc-hexane (6:1)

Sources & evidence

ORD record
ord-83379348b4c94eafaf59455c1df4b053
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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