Ethyl isothiocyanatoformate → N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide

HRID 999

Reaktionsgleichung

Reaktionsgleichung von HRID 999
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:23][C:24]([N:26]=[C:27]=[S:28])=[O:25])[CH3:22]>CN(C=O)C.C(OCC)(=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH:15][CH2:16][C:27]([NH:26][C:24]([O:23][CH2:21][CH3:22])=[O:25])=[S:28])[CH:12]=[CH:11][C:10]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 85320Ethyl isothiocyanatoformateHCID 19693799N-tert-Butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide

Produkt 1

HCID 54170420N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.20 g (4.0 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide is dissolved in 5 ml of anhydrous DMF, and 0.60 g (4.3 mmol) of 95% strength ethoxycarbonyl isothiocyanate is added. After 3 h at room temperature the mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The residue is taken up in a little ethyl acetate and precipitated with heptane at -25° C. The precipitate is filtered off with suction and dried to give 1.29 g (75% of theory) of colorless N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 110° C.

Aufarbeitung

  1. washwashed with 1N hydrochloric acid and water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed by distillation
  4. customprecipitated with heptane at -25° C
  5. filtrationThe precipitate is filtered off with suction
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-eb3a2bf3a97a4cecad374cf323a11215
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723409

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