2-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide → 2-(1-Phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharin

HRID 128704

Reaktionsgleichung

Reaktionsgleichung von HRID 128704
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=2[CH:15]([CH3:17])[CH3:16])[S:4]1(=[O:6])=[O:5].[Na].[C:21]1([N:27]2[C:31]([SH:32])=[N:30][N:29]=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[C:21]1([N:27]2[C:31]([S:32][CH2:2][N:3]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=4[CH:15]([CH3:17])[CH3:16])[S:4]3(=[O:6])=[O:5])=[N:30][N:29]=[N:28]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

4

Edukt 2

HCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 178527989HCID 178527989, Verbindung

Produkt 1

HCID 98897272-(1-Phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharinAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloromethyl-4-isopropyl-6-methoxysaccharin (0.25 g) and 1-phenyltetrazole-5-thiol sodium salt (0.173 g) in dimethylformamide (10 mL) was heated at 60°-80° C. for 8 hours, then poured into ice-water containing saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ether. The ether extract was washed with water and saturated aqueous sodium chloride, passed through silica gel and is stripped of ether affording 2-(1-phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharin as a foam (0.3 g, 83% yield).

Aufarbeitung

  1. temperaturewas heated at 60°-80° C. for 8 hours
  2. extractionThe resulting mixture was extracted with ether
  3. extractionThe ether extract
  4. washwas washed with water and saturated aqueous sodium chloride

Quellen und Nachweise

ORD-Eintrag
ord-ab3ebf0914af4952a968c7ec84693c55
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464852

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