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

HRID 266460

Reaktionsgleichung

Reaktionsgleichung von HRID 266460
[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 24 g of paraformaldehyde (0.8 mole) and 86.4 g of chlorotrimethylsilane (1.6 moles) in 200 mL of 1,2-dichloroethane was added 0.8 ml anhydrous tin(IV) chloride and the resulting solution stirred on a steam bath for one hour. 4-Isopropyl-6-methoxysaccharin (51.4 g, 0.2 mole) 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 50 mL of 2N sodium hydroxide solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by crystallization from ethyl acetate/hexane to give 57 g (87%) of 2-chloromethyl-4-isopropyl-6-methoxysaccharin, mp 151°.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe organic layer was separated
  3. washwashed with 50 mL of 2N sodium hydroxide solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by crystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a4a4d2119f1540299fbf11e8e6e35785
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650422

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