Formaldehyde → 2-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

HRID 129040

Reaktionsgleichung

Reaktionsgleichung von HRID 129040
[CH2:1]=[O:2].Cl[Si](C)(C)C.[Sn](Cl)(Cl)(Cl)[Cl:9].[CH:13]([C:16]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]2[C:17]=1[C:18](=O)[NH:19][S:20]2(=[O:22])=[O:21])([CH3:15])[CH3:14]>ClCCCl.O>[Cl:9][CH2:18][N:19]1[C:1](=[O:2])[C:17]2[C:23](=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:16]=2[CH:13]([CH3:15])[CH3:14])[S:20]1(=[O:22])=[O:21]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 6397ChlorotrimethylsilaneHCID 24287Tin tetrachlorideHCID 101473624-Isopropyl-6-methoxysaccharin

Produkt 1

HCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of paraformaldehyde (24 g) and chlorotrimethylsilane (86.4 g) in 1,2-dichloroethane (200 mL) was added dry tin(IV) chloride (0.8 mL) and the resulting solution was stirred on a steam bath for one hour. 4-Isopropyl-6-methoxysaccharin (51.4 g) was added to the clear solution and the mixture was refluxed for 18 hours, cooled to room temperature and poured into water. The organic layer was separated, washed with aqueous sodium hydroxide solution (2N, 50 mL), dried over magnesium sulfate and concentrated under vacuum. The residue was crystallized from ethyl acetate-hexane to give 2-chloromethyl-4-isopropyl-6-methoxysaccharin (57 g, 87% yield, m.p. 151° C.).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium hydroxide solution (2N, 50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was crystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1d78acb8944f484098c665ef939e6565
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466701

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