3-(Trifluoromethyl)phenyl isocyanate → 3-(3-Trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione

Methyl N-[1-(amino)-1-(methylthio)methylene]carbamate (14.8 g.) was dissolved in methylene chloride (150 ml.). 3-Trifluoromethylphenyl isocyanate (18.7 g.) was added to the solution during 5 minutes and the mixture was stirred at room temperature for 2.5 hours. A freshly prepared solution of sodium (2.3 g.) in methanol (20 ml.) was then added during 5 minutes and the subsequent mixture was stirred at room temperature for 16 hours. The mixture was then evaporated and the residue was dissolved in water (400 ml.). The aqueous solution obtained, was extracted with ethyl acetate (2×400 ml.) to remove neutral byproducts, and then acidified with concentrated hydrochloric acid to pH1. The solid which precipitated was separated by filtration, washed with water (3×500 ml.), and dried (over phosphorus pentoxide) to give 3-(3-trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione (25.9 g., 86%) as a white solid, m.p. 225°-228° C.

1. stirringthe subsequent mixture was stirred at room temperature for 16 hours
2. customThe mixture was then evaporated
3. dissolutionthe residue was dissolved in water (400 ml.)
4. customThe aqueous solution obtained
5. extractionwas extracted with ethyl acetate (2×400 ml.)
6. customto remove neutral byproducts
7. customThe solid which precipitated
8. customwas separated by filtration
9. washwashed with water (3×500 ml.)
10. dry with materialdried (over phosphorus pentoxide)

ORD-Eintrag

ord-4de95c22b07d4c588c9b466cc74a1852

Quelldatensatz

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04254122