Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Methyl 2-(4-methoxy-6-trifluoromethoxy-2-pyrimidinylaminocarbonylaminosulfonyl)benzoate

HRID 1974657

Reaktionsgleichung

Reaktionsgleichung von HRID 1974657
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])=[O:4].[NH2:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][C:27]([F:30])([F:29])[F:28])[N:19]=1>C(#N)C>[CH3:25][O:24][C:22]1[CH:21]=[C:20]([O:26][C:27]([F:29])([F:28])[F:30])[N:19]=[C:18]([NH:17][C:15]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:13])=[O:16])[N:23]=1

Komponenten

4

Edukt 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 150227204-Methoxy-6-(trifluoromethoxy)pyrimidin-2-amine

Produkt 1

HCID 15022726Methyl 2-(4-methoxy-6-trifluoromethoxy-2-pyrimidinylaminocarbonylaminosulfonyl)benzoateAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

4.8 g (0.02 mol) of 2-methoxycarbonylbenzenesulfonyl isocyanate in 10 ml of acetonitrile were added over the course of 15 minutes to a stirred mixture of 4.1 g (0.02 mol) of 2-amino-4-methoxy-6-trifluoromethoxypyrimidine and 100 ml of acetonitrile at 25° C., and the mixture was then stirred for 12 hours. The precipitate was removed (2.4 g of melting point 141°-143° C.) and then the filtrate was concentrated under reduced pressure and stirred with ether/petroleum ether, and the solid was filtered off with suction and dried. A further 4.3 g of the title compound of melting point 141°-143° C. were obtained. The total yield was 6.7 g (74.4% of theory).

Aufarbeitung

  1. customThe precipitate was removed (2.4 g of melting point 141°-143° C.)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringstirred with ether/petroleum ether
  4. filtrationthe solid was filtered off with suction
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6a3ddaacdcfb4b76b46f274a24d804b7
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283332

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