Hydrochloric Acid → Methyl 2-(methylthio)-4-ureidothiazole-5-carboxylate
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=1[NH2:12])=[O:4].ClS([N:17]=[C:18]=[O:19])(=O)=O.Cl.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:11][S:10][C:8]1[S:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([NH:12][C:18]([NH2:17])=[O:19])[N:7]=1Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
In 150 mL methylene chloride, 4-amino-2-methylthio-5-thiazolcarboxylic acid methyl ester (0.05 mol) was dissolved and cooled to −78° C. under nitrogen gas. Stirring, 0.07 mol (1.4 eq) of chlorosulfonyl isocyanate was added slowly to give a brown solution. The reaction was warmed slowly to 0° C. and a white precipitate forms. After 30 minutes, the solution was evaporated under vacuum, resuspended in 40 mL of 6N hydrochloric acid (4 eq) and heated to 100° C. After 30 minutes, the solution was cooled to room temp, neutralized with saturated sodium carbonate followed by saturated sodium bicarbonate. The white solid was isolated by filtration to give methyl 2-(methylthio)-4-ureidothiazole-5-carboxylate 76.
Aufarbeitung
- customto give a brown solution
- temperatureThe reaction was warmed slowly to 0° C.
- customthe solution was evaporated under vacuum
- temperatureheated to 100° C
- waitAfter 30 minutes
- temperaturethe solution was cooled to room temp
- customThe white solid was isolated by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-929f052087f64083bef5fa97bb2e1509
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158626B2
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