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

HRID 1439856

Reaktionsgleichung

Reaktionsgleichung von HRID 1439856
[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-958469ecbd8f4b42bd43a19b018246e4
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496815

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