Sodium Methoxide → 2-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazoline

HRID 22025Notes

Reaction equation

HRID 22025 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)[CH2:10][C:9](=[CH2:22])[S:8]1)=[O:5])[CH3:2].C[O-].[Na+]>C(O)C>[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]([CH3:22])[S:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 540384642-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

Product 1

HCID 538034182-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazolineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (2.0 g) and sodium methoxide (28 % methanolic solution; 1.2 g) in ethanol (50 ml) was refluxed for 30 minutes. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (200 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 1.6 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazoline (Compound No. 1).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. extractionthe concentrated residue was extracted with chlorofom (200 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-321cd103e8f946f58a94344346fe994f
Source dataset
uspto-grants-1995_06
Patent number
US05426188

Reaction notes

Loading…