2-Cyano-6-methoxy benzothiazole → 2-Cyano-6-hydroxybenzothiazole

HRID 539820

Reaktionsgleichung

Reaktionsgleichung von HRID 539820
C[O:2][C:3]1[CH:13]=[CH:12][C:6]2[N:7]=[C:8]([C:10]#[N:11])[S:9][C:5]=2[CH:4]=1.Cl.[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:13]=[CH:12][C:6]2[N:7]=[C:8]([C:10]#[N:11])[S:9][C:5]=2[CH:4]=1

Komponenten

3

Edukt 2

HCID 3421092-Cyano-6-methoxy benzothiazoleHCID 21584435Pyridinium hydrochloride

Produkt 1

HCID 98819122-Cyano-6-hydroxybenzothiazoleAusbeute 45 %

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of 6-methoxybenzo[d]thiazole-2-carbonitrile (1.0 g, 5.3 mmol) and dry pyridinium hydrochloride (11.3 g, 98.1 mmol) was stirred at 190° C. for 3 h. After the completion of reaction, it was cooled to room temperature to obtain a yellow solid. This solid was purified by flash chromatography (silica gel, methylene chloride/ethyl acetate=25/1) to afford 6-hydroxybenzo[d]thiazole-2-carbonitrile as a yellow solid (0.42 g, 45%). 1H-NMR (DMSO-d6, 300 MHz): δ 10.20 (s, 1H), 8.70 (m, 1H), 8.45 (m, 1H), 8.10 (m, 1H) ppm; MS (ESI): 177.1 (M+1).

Aufarbeitung

  1. customAfter the completion of reaction, it
  2. temperaturewas cooled to room temperature
  3. customto obtain a yellow solid
  4. customThis solid was purified by flash chromatography (silica gel, methylene chloride/ethyl acetate=25/1)

Quellen und Nachweise

ORD-Eintrag
ord-132966f7e0e349f9a57b2bcf75373325
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871770B2

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