Diethyl Ether → Sulindac sulfone methyl ester

HRID 379630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379630
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:20])=[O:19])=[CH:14][CH:13]=1)/[C:6]([CH3:21])=[C:5]2[CH2:22][CH2:23]N(O)C(N)=O.ClC1C=C(C=CC=1)[C:33](OO)=[O:34].[OH-:40].[Ca+2].[OH-:42].CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:20])(=[O:40])=[O:19])=[CH:14][CH:13]=1)/[C:6]([CH3:21])=[C:5]2[CH2:22][C:23]([O:34][CH3:33])=[O:42]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 10222622(Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylsulfinylbenzylidene)inden-3-yl]ethyl}-N-hydroxy urea

Produkt 1

HCID 9952140Sulindac sulfone methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl (Z)-5-fluoro-2-methyl-1-(4-methylsulfinyl benzylidene)inden-3-yl acetate from Example 7 (3.7 g, 10 mmol) in methylene chloride (100 mL) there was added 85% m-chloroperoxy benzoic acid (2.54 g, 12.5 mmol) and the mixture was stirred at room temperature for 1 hour. There was added more methylene chloride (100 mL) then calcium hydroxide (5.5 g) and after 10 minutes, the suspension was filtered. The residue obtained by evaporation of the filtrate was stirred with ether (100 mL) at room temperature for 5 hours, then filtered to afford the title compound as a fluffy yellow solid, mp 162-164° C.

Aufarbeitung

  1. filtrationthe suspension was filtered
  2. customThe residue obtained by evaporation of the filtrate
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f2a138f2ff694eb79b1c8bf3f13b4f02
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300346B1

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