Dimethylformamide → 3-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 5833

Reaktionsgleichung

Reaktionsgleichung von HRID 5833
[NH:1]1[C:6](=[O:7])[CH2:5][S:4][C:3]2[CH:8]=[CH:9][C:10]3[C:15]([C:2]1=2)=[CH:14][CH:13]=[CH:12][CH:11]=3.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C[O-].[Na+].CN(C)C=O>O>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:5]2[S:4][C:3]3[CH:8]=[CH:9][C:10]4[C:15]([C:2]=3[NH:1][C:6]2=[O:7])=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 77264-ChlorobenzaldehydeHCID 10942334Sodium MethoxideHCID 138234521H-Naphtho[2,1-b][1,4]thiazin-2(3H)-one

Produkt 1

HCID 537645223-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-oneAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (5.17 g), 4-chlorobenzaldehyde (5.62 g), sodium methoxide (1.73 g) and dimethylformamide (80 ml) is refluxed for 4.5 hours. After cooling, the reaction mixture is poured into water and the resulting precipitate is separated by filtration, washed and dried and then is recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (4.28 g). M.p. 277°-279° C.

Aufarbeitung

  1. temperatureis refluxed for 4.5 hours
  2. temperatureAfter cooling
  3. customthe resulting precipitate is separated by filtration
  4. washwashed
  5. customdried
  6. customis recrystallized from tetrahydrofuran-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f9dddaae649d44ff923cca915bde63f6
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246929

Verknüpfte Notizen

Wird geladen…