O-Xylene → 2-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

HRID 2292871Notes

Reaction equation

HRID 2292871 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:9]([CH2:13][C:14](Cl)=[CH2:15])[C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.C1(C)C(C)=CC=CC=1.C(=O)([O-])O.[K+]>[Cl-].[Zn+2].[Cl-].O>[NH:12]=[C:10]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)[CH2:13][C:14](=[CH2:15])[S:11]1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 516893Potassium BicarbonateHCID 11130193N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea

Product 1

HCID 152396762-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidineYield 74.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea (2.94 g) and zinc chloride (6.08 g) were added to xylene (50 ml) at room temperature, and the mixture was heated to 90° C. and stirred at the same temperature for 1.5 hour. After cooling, water was added to the reaction mixture, which was neutralized by addition of potassium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, and the residual oil was subjected to preparative liquid chromatography, which afforded 1.92 g of 2-imino-3-(3-(trifluoromethyl)phenyl)-5-methylidenethiazolidine (74% yield). From the results of analysis by liquid chromatography, the purity was determined to be not lower than 99%.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1f699e3f326d40c0ab71fa7ef81e2a2e
Source dataset
uspto-grants-1997_11
Patent number
US05684196

Reaction notes

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