Potassium Cyanide → 2-Cyano-6-ethylaminobenzothiazole

HRID 1511491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511491
[C-:1]#[N:2].[K+].Cl[C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][CH2:15][CH3:16])[CH:11]=[CH:10][C:8]=2[N:9]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][CH2:15][CH3:16])[CH:11]=[CH:10][C:8]=2[N:9]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 9032Potassium CyanideHCID 62657Potassium Phosphate, TribasicHCID 670401072-Chloro-6-ethylaminobenzothiazole

Produkt 1

HCID 670407172-Cyano-6-ethylaminobenzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Potassium cyanide (18 mg) and 2-chloro-6-ethylaminobenzothiazole (18 mg) were dissolved in 1 ml DMSO and heated to 120° C. for 4 h. After cooling to room temperature, the reaction was poured into 0.2M potassium phosphate, pH 4.5. The aqueous layer was extracted with ethyl acetate three times, washed with water, and dried over sodium sulfate. The solvent was removed by rotary evaporation and the residue purified by silica gel chromatography (20% ethyl acetate in hexanes). 1H-NMR (d6-DMSO): δ 7.85 (d, 1H, J=9.2 Hz), 7.13 (d, 1H, J=2.4 Hz), 6.98 (dd, 1H, J=2.4, 8.8 Hz), 6.44 (br t, 1H), 3.09 (m, 2H), 1.18 (t, 3H, J=7.2 Hz).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate three times
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed by rotary evaporation
  6. customthe residue purified by silica gel chromatography (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-62da027dd8ab4e78867b969337d77c93
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216550B2

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