Sodium Hydroxide → 2-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazole

HRID 131621

Reaktionsgleichung

Reaktionsgleichung von HRID 131621
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:20])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[OH-].[Na+]>O.C(O)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[F:1][C:2]1[C:3]2[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[S:20][C:4]=2[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 11702019HCID 11702019, Verbindung

Produkt 1

HCID 117019992-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazoleAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178511488HCID 178511488, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A solution of N-(2-fluorophenyl)-3,4-dimethoxythiobenzamide (0.850 g, 2.92 mmol) and sodium hydroxide (0.93 g, 23.3 mmol) in water (10 mL) and ethanol (0.5 mL) was added dropwise to a solution of potassium ferricyanide (3.84 g, 11.7 mmol) in water (5 mL) at 95° C. The resulting solution was stirred at 95° C. for a further 2 h and then cooled in an ice bath. The precipitate was collected by vacuum filtration, washed with water and dissolved in ethyl acetate (10 mL) and insoluble material was removed by filtration. The filtrate was concentrated in vacuo and the crude product purified by column chromatography (dichloromethane) to give the required product as a pale yellow powder (0.46 g, 55% yield), mp 129° C.; 1H NMR (DMSO-d6) δ 7.95 (1H, m, ArH), 7.65 (2H, m, ArH), 7.42 (2H, m, ArH), 7.15 (1H, m, ArH), 3.90 (3H, s, OMe), 3.88 (3H, s, OMe); m/z (CI) 290 (M++1); Anal. (C15H12FNO2S) C, H, N. C: found 62.36%, calc. 62.27%; H: found 4.19%, calc.4.18%; N: found 4.93%, calc. 4.84%.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate (10 mL)
  5. custominsoluble material was removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude product purified by column chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-4ad773408e8644349028421071ca49fb
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384966B2

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