Sulfuric Acid → 1-Amino-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 380315

Reaktionsgleichung

Reaktionsgleichung von HRID 380315
S(=O)(=O)(O)O.[NH2:6][N:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10](=[O:17])[N:9]([C:18]2[CH:23]=[C:22]([O:24]C(C)C)[C:21]([Cl:28])=[CH:20][C:19]=2[F:29])[C:8]1=[O:30]>C(Cl)Cl.O>[NH2:6][N:7]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10](=[O:17])[N:9]([C:18]2[CH:23]=[C:22]([OH:24])[C:21]([Cl:28])=[CH:20][C:19]=2[F:29])[C:8]1=[O:30]

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 184029211-Amino-3-(4-chloro-2-fluoro-5-isopropyloxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Produkt 1

HCID 184029831-Amino-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Conc. sulfuric acid (3 ml) was added to a solution of 1-amino-3-(4-chloro-2-fluoro-5-isopropyloxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (4.5 g) in methylene chloride (50 ml) stirred at 0° C. After 1 hour the mixture was diluted with water and processed. The oily product was chromatographed on silica gel eluting with ethyl acetate:hexane, 2:3, to give 1-amino-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione as a pale yellow amorphous solid (3.6 g,) 1H NMR (CDCl3, TMS): 7.27(1H, d, J=8.8 Hz), 6.88(1H, d, J=6.5 Hz), 6.28(1H, s), 5.86(1H, br. s), 4.61(2H, s).

Aufarbeitung

  1. customThe oily product was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-80da9aeffe58445a9582c5809aeaeae4
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303543B1

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