Methyl iodide → 6-Iodo-2-(methylthio)benzo[d]thiazole

HRID 1691980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691980
[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>O1CCCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH3:12])[S:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178527793HCID 178527793, Verbindung

Produkt 1

HCID 669058856-Iodo-2-(methylthio)benzo[d]thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred, room temperature mixture of 6-iodobenzo[d]thiazole-2-thiol (Reference Example 6a, 1.5 g, 5.1 mmol) and potassium carbonate (0.707 g, 5.1 mmol) in tetrahydrofuran (30 mL) was added methyl iodide (0.35 mL, 5.6 mmol). The reaction mixture was stirred at room temperature overnight, then volatiles were removed under reduced pressure to give a solid. The solid was partitioned between saturated aqueous sodium carbonate and chloroform. The chloroform layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide 6-iodo-2-(methylthio)benzo[d]thiazole. 1H NMR (300 MHz, CDCl3) δ ppm 2.78 (s, 3H), 7.58 (d, J=9 Hz, 1H), 7.69 (dd, J=2, 9 Hz, 1H), 8.07 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 308 (M+H)+.

Aufarbeitung

  1. customvolatiles were removed under reduced pressure
  2. customto give a solid
  3. customThe solid was partitioned between saturated aqueous sodium carbonate and chloroform
  4. dry with materialThe chloroform layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a795a577bf73401c9dc0e86e1fbd6ba4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153813B2

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