O-Phenylenediamine → 2-(1H-Benzimidazol-2-yl)-1,3-benzothiazole

HRID 324917

Reaktionsgleichung

Reaktionsgleichung von HRID 324917
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17].[S]>N1C=CC=CC=1.[Cl-].[Na+].O>[NH:17]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:18]=[C:1]1[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

6

Edukt 3

HCID 7243O-PhenylenediamineHCID 84462-MethylbenzothiazoleHCID 5362487Sulfur

Produkt 1

HCID 3738782-(1H-Benzimidazol-2-yl)-1,3-benzothiazoleAusbeute 13,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The heterogeneous mixture consisting of methylbenzothiazole (59.6 g, 0.4 mol), ortho-phenylenediamine (43.2 g, 0.4 mol) and sulfur (38.4 g, 1.2 mol) in 300 ml of pyridine was heated at the reflux point of pyridine for 22 hours. The reaction mixture was cooled and poured into a solution of brine. After extraction with ethyl acetate, washing of the organic phase 3 times with water, drying over sodium sulfate and concentration of the solvent under vacuum, the solid obtained was washed with acetone. After drying, 2-(1H-benzimidazol-2-yl)benzothiazole (13.8 g, yield: 13%) was obtained in the form of a yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionAfter extraction with ethyl acetate
  3. washwashing of the organic phase 3 times with water
  4. dry with materialdrying over sodium sulfate and concentration of the solvent under vacuum
  5. customthe solid obtained
  6. washwas washed with acetone
  7. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-2d6cc20732844b04a3fbfb1784cb370e
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221343B1

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