1-Butanol → 2,1,3-Benzothiadiazole

HRID 1057088

Reaktionsgleichung

Reaktionsgleichung von HRID 1057088
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.C1(N(C2C=CC(B(O)O)=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCC>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:7]1[S:8][N:9]=[C:10]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=12

Komponenten

8

Edukt 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 675022,1,3-Benzothiadiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4,7-dibromobenzo[2,1,3]thiadiazole (13.2 g, 45 mmol), 4-(N,N-diphenylamino)phenylboronic acid (30.0 g, 104 mmol), a solution of sodium carbonate (21.2 g, 200 mmol) in water (80 mL), tetrakis(triphenylphosphine)palladium(0) (5.0 g, 4.3 mmol), n-butanol (800 mL), and toluene (400 mL) was stirred under argon and heated at 100° C. for 20 hours. After cooling to room temperature, the mixture was diluted with water (600 mL) and stirred for 2 hours. Finally, the reaction mixture was extracted with toluene (2 L), and the volatiles were removed under reduced pressure. The residue was chromatographed using silica gel and hexane/dichloromethane (1:1) as an eluent to give 26.96 g (43.3 mmol, 96%) of 4,7-bis[(N,N-diphenylamino)phenyl)]benzo[2,1,3]thiadiazole (Intermediate A).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionFinally, the reaction mixture was extracted with toluene (2 L)
  3. customthe volatiles were removed under reduced pressure
  4. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-4ea184599ce442c68f305d5075c1b48c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399730B2

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