1-Amino-2-naphthalenethiol → 3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 1198440

Reaktionsgleichung

Reaktionsgleichung von HRID 1198440
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[SH:12].[BH4-].[Na+].C([O-])(=O)C.[Na+].Br[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:22](OC)=[O:23]>C(O)C.C(O)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:21]2[S:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11]([C:2]=3[NH:1][C:22]2=[O:23])=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 1133141-Amino-2-naphthalenethiolHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Produkt 1

HCID 189844403-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-bromo-4-chlorophenylacetate (46.8 g), and the mixture is sitrred at room temperature under argon overnight. The reaction mixture is poured into ice water and the resulting precipitate is separated by filtration, washed, dried and recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals.

Aufarbeitung

  1. waitthe mixture is sitrred at room temperature under argon overnight
  2. customthe resulting precipitate is separated by filtration
  3. washwashed
  4. customdried
  5. customrecrystallized from tetrahydrofuran-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4e723883002e4d7b86b8bb54c9017582
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281592

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