Benzonitrile → 2-Aminobenzothiazole-6-carbonitrile

HRID 9100

Reaktionsgleichung

Reaktionsgleichung von HRID 9100
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[K+].BrBr.C(#N)C1C=CC=CC=1>C(O)(=O)C.O>[NH2:12][C:11]1[S:10][C:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=2[N:1]=1

Komponenten

7

Edukt 4

HCID 7505BenzonitrileHCID 133964-AminobenzonitrileHCID 24408BromineHCID 516872Potassium thiocyanate

Produkt 1

HCID 43271392-Aminobenzothiazole-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

4-Aminobenzonitrile is dissolved in acetic acid (or a weak protic acid) and the solution is cooled to about 16–30° C., preferably 16–18° C. Potassium thiocyanate is added and the flask is then equipped with an addition funnel. The addition funnel is charged with bromine and acetic acid. This dark solution is then added to the benzonitrile solution in a dropwise fashion under good agitation and allowed to stir for about 12–20 hours, preferrably about 16 hours. The slurry is then drowned into water and filtered. The presscake is washed well with water, reslurried in dilute aqueous alkali and filtered. Again the presscake is washed well with water to obtain the title compound.

Aufarbeitung

  1. temperatureis cooled to about 16–30° C., preferably 16–18° C
  2. customthe flask is then equipped with an addition funnel
  3. filtrationfiltered
  4. washThe presscake is washed well with water
  5. filtrationfiltered
  6. washAgain the presscake is washed well with water

Quellen und Nachweise

ORD-Eintrag
ord-6eca5615015f4ce68df2769bea908bce
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091227B2

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