Potassium tert-butoxide → 2-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

HRID 22032Notes

Reaction equation

HRID 22032 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][CH:9]([CH2:22]Br)[S:8]1)=[O:5])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)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)[CH2:10][C:9](=[CH2:22])[S:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 536349452-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine

Product 1

HCID 540384642-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidineYield 44.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A.solution of 2-ethoxycarbonylimino-3-(3-tri-fluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours, and the solvent was distilled off under reduced pressure. The residue was extracted with chloroform (100 ml), washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography to give 0.25 g of 2-ethoxycarbonylimino-3-(3-trifluoromethyl-phenyl)-5-methylenethiazolidine (Compound (i)).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with chloroform (100 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of the solvent

Sources & evidence

ORD record
ord-5505bdf514d3417f835495e1e3c4378c
Source dataset
uspto-grants-1995_06
Patent number
US05426188

Reaction notes

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