Reaktionsgleichung
[N+:1]([CH:4]=[C:5]1[NH:10][CH2:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].C(N(C(C)C)C(C)C)C.C(Cl)Cl.[CH2:23]([S:35](Cl)(=[O:37])=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O>[CH2:23]([S:35]([N:10]1[CH2:9][CH2:8][CH2:7][S:6][C:5]1=[CH:4][N+:1]([O-:3])=[O:2])(=[O:37])=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]Komponenten
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
1.6 g of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine, 3.18 g of ethyldiisopropylamine and 20 ml of methylene chloride were mixed. The mixture was cooled to and stirred at -60° C. under a nitrogen atmosphere while 2.95 g of dodecanesulfonyl chloride was added in portions over a 10 minute period. The mixture was allowed to warm to 10° C. (2.5 hours), then stirred at 10° C. for 1 hour and at 20° C. for 1.5 hours. The resulting mixture was poured into water, and the organic phase was separated, dried (MgSO4), filtered and stripped of solvent. The residue, a gum, was chromatographed over silica gel, using methylene chloride as eluent. After workup the product was recrystallized from ethanol to give N-(dodecylsulfonyl)-2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (3A) as a solid, m.p.: 116°-117° C.
Aufarbeitung
- temperatureThe mixture was cooled to and
- additionwas added in portions over a 10 minute period
- customthe organic phase was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe residue, a gum, was chromatographed over silica gel
- customwas recrystallized from ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-b1afed8fd099419786edb1cc6b2f27d9
- Quelldatensatz
- uspto-grants-1984_12
- Patentnummer
- US04486427
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