Methyl iodide → N-(3-Chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1730569
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[NH:14][S:15](=[O:29])(=[O:28])[C:16]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:17]=3[C:18]=2[OH:19])=[O:12])[CH:7]=[CH:8][CH:9]=1.[CH3:30]I>CO>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[N:14]([CH3:30])[S:15](=[O:28])(=[O:29])[C:16]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:17]=3[C:18]=2[OH:19])=[O:12])[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 54695941N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide

Produkt 1

HCID 54695958N-(3-Chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3.15 ml of 1 N sodium hydroxide (3.15 millimols) were added dropwise to a suspension of 1.2 gm (3 millimols) of N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 100 ml of methanol and 1.7 gm (12 millimols) of methyl iodide. The resulting mixture was stirred at room temperature for 72 hours, and was then evaporated to dryness in vacuo. The residue was washedwith a small quantity of water, and the remaining solid matter was recrystallized from ethylene chloride, yielding 0.8 gm (64% of theory) of N-(3-chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 248°-249° C (decomp.).

Aufarbeitung

  1. customwas then evaporated to dryness in vacuo
  2. customthe remaining solid matter was recrystallized from ethylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-b43cd8d106054a39b300429aa6b11627
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03992535

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