2-Aminothiazole → HCID 59732845, Verbindung

HRID 131781

Reaktionsgleichung

Reaktionsgleichung von HRID 131781
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[O:8]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C.[NH2:31][C:32]1[S:33][CH:34]=[CH:35][N:36]=1>O1CCCC1>[O:8]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH:17][S:2]([NH:5][C:6]([NH:31][C:32]1[S:33][CH:34]=[CH:35][N:36]=1)=[O:7])(=[O:4])=[O:3])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 21552-AminothiazoleHCID 70918Chlorosulfonyl isocyanateHCID 75899Benzenamine, 2-phenoxy-HCID 81531Diisopropylethylamine

Produkt 1

HCID 59732845HCID 59732845, VerbindungAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of chlorosulfonyl isocyanate (0.22 ml, 2.5 mmol) in tetrahydrofuran (25 ml) were added 2-phenoxyaniline (0.37 g, 2.0 mmol) and DIEA (0.89 ml, 5.0 mmol) at −78° C. The solution was stirred and slowly allowed to warmed up to 0° C. To this reaction mixture, was added 2-amino thiazole (0.20 g, 2.0 mmol) and continued stirring at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (ethylacetate:hexanes, from 50:50 to 90:10 as eluent system) to afford the title compound (0.52 g, 66%).

Aufarbeitung

  1. stirringcontinued stirring at room temperature for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography (ethylacetate:hexanes, from 50:50 to 90:10 as eluent system)

Quellen und Nachweise

ORD-Eintrag
ord-ea21d34cde694f24984f22731d625b19
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384967B2

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