Chloroform → N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1730578
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]=2[S:5](=[O:17])(=[O:16])[NH:4][C:3]=1[C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3.[CH:21]([Cl:24])(Cl)Cl.[H][H]>[Pd].CO>[Cl:24][C:21]1[CH:18]=[C:3]([NH:20][C:18]([C:3]2[NH:4][S:5](=[O:17])(=[O:16])[C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:19])[CH:2]=[CH:7][CH:6]=1

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 681429134-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54695941N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 490 mgm (1 millimol) of 2-benzyl-N-3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 100 ml of a mixture of chloroform and methanol (2:1) was hydrogenated in the presence of 500 mgm of a palladium-on-charcoal catalyst (10%) at a hydrogen pressure of 3 atmospheres for 10 hours. The reaction mixture was then filtered, and the catalyst left on the filter was copiously washed with hot chloroform. The combined filtrates were evaporated, and the residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm), using chloroform/methanol (20:1) as the eluant. 230 mgm (57% of theory) of N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 262° C (decomp.), were obtained.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. waitthe catalyst left on the filter
  3. washwas copiously washed with hot chloroform
  4. customThe combined filtrates were evaporated
  5. customthe residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm)

Quellen und Nachweise

ORD-Eintrag
ord-a644cc8250bf4c7cb2cccf8c5d6c32d8
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03992535

Notizen zur Reaktion

Wird geladen…