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

HRID 265731Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea (1.47 g) and stannic chloride n-hydrate (n=4 to 5) (0.09 g) were added to methyl isobutyl ketone (7.50 g) at room temperature, and the mixture was heated to 90° C. and stirred at the same temperature for 7 hours. After cooling, 35% hydrochloric acid (0.52 g) was added to the reaction mixture with stirring, and the mixture was heated to 90° C. and stirred at the same temperature for 2.5 hours. After cooling, water was added to the reaction mixture, which was then neutralized by addition of sodium hydrogen carbonate and extracted with methyl isobutyl ketone. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, which afforded 1.08 g of 2-imino-3-(3-(trifluoromethyl)phenyl)-5-methyl-4-thiazoline (75% yield as a corrected value from the below-mentioned purity). From the results of analysis by liquid chromatography, the purity was determined to be 89%.

Workup

temperatureAfter cooling
stirringwith stirring
temperaturethe mixture was heated to 90° C.
stirringstirred at the same temperature for 2.5 hours
temperatureAfter cooling
extractionextracted with methyl isobutyl ketone
washThe organic layer was washed with water
customThe solvent was removed by distillation under reduced pressure, which

Sources & evidence

ORD record: ord-7de85d6200494bfca08080e34319508c
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648533

Reaction notes

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