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

HRID 265727Notes

Reaction equation

HRID 265727 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-416f336d410e48f199fc7761cab180ff
Source dataset
uspto-grants-1997_07
Patent number
US05648533

Reaction notes

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