p-Toluenesulfonic acid → 6-Bromo-1-methyl-1H-benzimidazole

HRID 1507024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507024
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[CH:9][N:8]([CH3:11])[C:6]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 121982705-BROMO-N1-METHYLBENZENE-1,2-DIAMINE

Produkt 1

HCID 235376446-Bromo-1-methyl-1H-benzimidazoleAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9005Trimethyl orthoformateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36 g, 1.9 mmol). The reaction mixture was heated at 100° C. for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93%) MS (ESI+) e/z: 212.1.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was used in next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-99ede51be86e4ac5a36a3c9dd3c68f11
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221794B2

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