1,1-Dibromoethane → 2-Imino-3-(3-trifluoromethylphenyl)thiazolidine

HRID 5325

Reaction equation

HRID 5325 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.Br[CH:16](Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH:12]=[C:10]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[CH2:17][CH2:16][S:11]1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 7358443-(Trifluoromethyl)phenylthiourea

Product 1

HCID 224169782-Imino-3-(3-trifluoromethylphenyl)thiazolidineYield 110%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-(3-trifluoromethylphenyl)thiourea (6.1 g), dibromoethane (5.7 g) and anhydrous potassium carbonate (11.5 g) in acetone (60 ml) was refluxed for 1 day. The solvent was removed by distillation therefrom, and the residue was extracted with ethyl ether, washed with water, dried over anhydrous magnesium sulfate and subjected to column chromatography to give 7.5 g of 2-imino-3-(3-trifluoromethylphenyl)thiazolidine. The thus obtained 2-imino-3-(3-trifluoromethylphenyl)thiazolidine (1.0 g), n-butyl chlorocarbonate (0.61 g) and triethylamine (1.2 g) were dissolved in tetrahydrofuran, and the resultant solution was stirred at room temperature for 5 hours. The solvent was removed, and the residue was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography to give 0.57 g of 2-butoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazolidine.

Workup

  1. customThe solvent was removed by distillation
  2. extractionthe residue was extracted with ethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-7abe0b247b3646b18c986acb76de854f
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Linked notes

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