Benzyl Bromide → 2-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin

HRID 1957441

Reaktionsgleichung

Reaktionsgleichung von HRID 1957441
[Cs].C(C1C=C(O)C=C2C=1C(=O)NS2(=O)=O)(C)C.C(Br)C1C=CC=CC=1.[CH2:26]([N:33]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][C:39]([OH:48])=[CH:40][C:41]=2[CH:45]([CH3:47])[CH3:46])[S:34]1(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:49]([N:51]([CH2:55][CH3:56])[C:52](Cl)=[S:53])[CH3:50]>CN(C=O)C>[CH2:26]([N:33]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][C:39]([O:48][C:52](=[S:53])[N:51]([CH2:55][CH3:56])[CH2:49][CH3:50])=[CH:40][C:41]=2[CH:45]([CH3:46])[CH3:47])[S:34]1(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

7

Edukt 5

HCID 7498Benzyl BromideHCID 66607Diethylthiocarbamoyl chlorideHCID 5354618CesiumHCID 100373464-Isopropyl-6-hydroxysaccharinHCID 700446502-Benzyl-4-isopropyl-6-hydroxysaccharin

Produkt 1

HCID 867465622-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Selective N-benzylation of the cesium salt of 4-isopropyl-6-hydroxysaccharin (Preparation 19) with benzyl bromide and reaction of the 2-benzyl-4-isopropyl-6-hydroxysaccharin with N,N-diethylthiocarbamyl chloride in DMF using the procedure described above in Preparation 12 affords 2-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin which, on heating, rearranges to 2-benzyl-4-isopropyl-6-(N,N-diethylcarbamyl-thio)saccharin. The latter, on hydrolysis with alkali, affords 2-benzyl-4-isopropyl-6-mercaptosaccharin which on reaction with methyl iodide, and transfer hydrogenolysis affords 4-isopropyl-6-methylthiosaccharin. Oxidation of the latter with one or two molar equivalents of 3-chloroperbenzoic acid affords 4-isopropyl-6-methyl-sulfinylsaccharin and 4-isopropyl-6-methylsulfonylsaccharin.

Aufarbeitung

  1. customdescribed above in Preparation 12

Quellen und Nachweise

ORD-Eintrag
ord-b88a8425df884e628a17ce55bbde03ef
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05783589

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