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

HRID 5309Notes

Reaction equation

HRID 5309 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)[CH:10]=[C:9]([CH3:22])[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 538034182-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazolineYield 64%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (100 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 0.36 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 (100 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-559f69803bbe4b658724c6bc142b64a7
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Reaction notes

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