Thionyl Chloride → N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl urea
Reaktionsgleichung
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[O:9])[C:4](=[O:22])[CH2:3]1.O[NH:24][C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26].S(Cl)(Cl)=O>O1CCOCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([S:19]([NH:24][C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])(=[O:21])=[O:20])=[CH:17][CH:18]=2)=[O:9])[C:4](=[O:22])[CH2:3]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
0.6 g of 4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfinic acid (crude product m.p. 113°-115° C., prepared by reaction of 4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfochloride with sodium sulfite) and 0.3 g of N-hydroxy-N'-butyl urea are dissolved in 50 ml of dioxan. 0.4 g of thionyl chloride in 10 ml of dioxan is added dropwise to this solution, and the batch is heated for 2 hours at 60° C. Subsequently, the solvent is evaporated under reduced pressure, water is added dropwise to the residue, the oily substance is separated and reprecipitated from ammonia. The N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl urea obtained has a melting point of 155°-157° C., and, with the substance obtained according to Example 8, shows no depression.
Aufarbeitung
- customSubsequently, the solvent is evaporated under reduced pressure, water
- additionis added dropwise to the residue
- customthe oily substance is separated
- customreprecipitated from ammonia
Quellen und Nachweise
- ORD-Eintrag
- ord-a859a06453f64f2aaadcec60d2475987
- Quelldatensatz
- uspto-grants-1983_04
- Patentnummer
- US04379785
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