N-Iodosuccinimide → 2-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-iodothiazoline

HRID 22030

Reaction equation

HRID 22030 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:10]=[CH:9][S:8]1)=[O:5])[CH3:2].[I:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]=[C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[CH:10]=[C:9]([I:22])[S:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 543520892-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline

Product 1

HCID 539747642-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-iodothiazolineYield 14.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline (0.5 g) and N-iodosuccinimide (0.4 g) in chloroform (30 ml) was refluxed for 20 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.1 g of 2-ethoxycarbonylimino-3-(3-tri-fluoromethylphenyl)-5-iodothiazoline (Compound No. 42).

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with an aqueous sodium sulfite solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-72ae534445ea4f8694ce3e8f636918ed
Source dataset
uspto-grants-1995_06
Patent number
US05426188

Linked notes

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