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Benzothiazole → 2-(Tributylstannyl)-1,3-benzothiazole

HRID 1433846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433846
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>O1CCCC1>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[CH2:25][CH2:26][CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7222BenzothiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 37623922-(Tributylstannyl)-1,3-benzothiazoleAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of benzothiazole (30.7 g) in tetrahydrofuran (700 ml), which was cooled at −78° C., was added dropwise n-butyllithium (2.5M solution in hexane) (100 ml) under a nitrogen atmosphere, the solution was stirred for 10 minutes at −78° C. Tributyltin chloride (77.9 g) was added dropwise thereto, the solution was stirred for 1.5 hours at −78° C., and then stirred for 2 hours while warming from −78° C. to room temperature. The reaction mixture was concentrated in vacuo, diethyl ether (400 ml) was added thereto, insoluble material was removed by filtration, and then the solvent was evaporated in vacuo. The residue was purified by distillation in vacuo (0.5 mmHg, 170 to 184° C.) to provide the title compound (73.0 g).

Aufarbeitung

  1. stirringthe solution was stirred for 1.5 hours at −78° C.
  2. stirringstirred for 2 hours
  3. temperaturewhile warming from −78° C. to room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo, diethyl ether (400 ml)
  5. additionwas added
  6. custominsoluble material was removed by filtration
  7. customthe solvent was evaporated in vacuo
  8. distillationThe residue was purified by distillation in vacuo (0.5 mmHg, 170 to 184° C.)

Quellen und Nachweise

ORD-Eintrag
ord-6cb384d47d4b4554a4e2cddfbf8cda0d
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612114B2

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