Sulfuric Acid → 2(3H)-Thiazolimine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-

HRID 2292868Notes

Reaction equation

HRID 2292868 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.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>[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)[CH:13]=[C:14]([CH3:15])[S:11]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 11130193N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea

Product 1

HCID 110215462(3H)-Thiazolimine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-Yield 95.3%

Conditions

Temperature
90 °C

Procedure

N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea (1.00 g) was added to 98% sulfuric acid (9.96 g) at room temperature with stirring, and the mixture was heated to 90° C. and stirred at the same temperature for 1.0 hour. After cooling, ice-water was added to the reaction mixture, which was then neutralized by addition of sodium carbonate and extracted with ethyl acetate. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, which afforded 0.835 g of 2-imino-3-(3-(trifluoromethyl)phenyl)-5-methyl-4-thiazoline as an oil (81% yield as a corrected value from the below-mentioned purity). From the results of analysis by liquid chromatography, the purity was determined to be 85%.

Workup

  1. stirringstirred at the same temperature for 1.0 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record
ord-9c9173085c26473986cc00474fde8ee4
Source dataset
uspto-grants-1997_11
Patent number
US05684196

Reaction notes

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