Diisopropylethylamine → HCID 70059641, Verbindung

HRID 266487Notizen

Reaktionsgleichung

C(N(C(C)C)CC)(C)C.[CH:10]([C:13]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]2[C:14]=1[C:15](=[O:28])[NH:16][S:17]2(=[O:19])=[O:18])([CH3:12])[CH3:11].[C:29]1([S:35][CH2:36]Cl)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O.C(OCC)(=O)C>[C:29]1([S:35][CH2:36][N:16]2[C:15](=[O:28])[C:14]3[C:20](=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3:25])=[CH:23][C:13]=3[CH:10]([CH3:12])[CH3:11])[S:17]2(=[O:18])=[O:19])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Diisopropylethylamine (0.5 mL) was added to a solution of 4-isopropyl-6,7-dimethoxysaccharin (0.5 g) in dimethylformamide (3 mL). After 15 minutes chloromethyl phenyl sulfide (0.35 g) was added. The mixture was heated at 80° C. for 16 hours, diluted with ethyl acetate, washed with aqueous sodium carbonate solution, hydrochloric acid (3N) and saturated aqueous sodium chloride solution, dried over sodium sulfate, and stripped of solvents. Purification of the residue by flash chromatography on silica gel using dichloromethane as eluant gave 2-phenylthiomethyl-4-isopropyl-6,7-dimethoxysaccharin (0.35 g), chlorination of which with sulfuryl chloride (0.1 mL) in dichloromethane (3 mL) and purification of the product by trituration with hexane gave 2-chloremethyl-4-isopropyl-6,7-dimethoxysaccharin, 0.3 g.

Aufarbeitung

washwashed with aqueous sodium carbonate solution, hydrochloric acid (3N) and saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
customPurification of the residue by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-d585029694fc416c843ef1b55c27f0a5
Quelldatensatz: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05650422

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