Potassium Hydroxide → 2-(1H-imidazol-2-yl)-4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazole

HRID 1244383

Reaktionsgleichung

Reaktionsgleichung von HRID 1244383
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)=[S:17].[OH-].[K+]>O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+6]>[NH:22]1[CH:21]=[CH:20][N:19]=[C:18]1[C:16]1[S:17][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[N:15]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 865950071H-imidazole-2-carbothioic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide

Produkt 1

HCID 1358567812-(1H-imidazol-2-yl)-4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazoleAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11963580Ferrate(4-), hexakis(cyano-C)-, tetrapotassium, (OC-6-11)-KatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

0.085 g of 1H-Imidazole-2-carbothioic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (0.27 mmol) was taken up in water (6.0 ml) and treated with 0.06 g KOH (1.07 mmol) and 0.331 g of potassium hexacyano ferrate (1.0 mmol) at reflux for 16 h. After cooling to ambient temperature water (10 ml) was added and the reaction mixture was extracted with methylene chloride and dried over sodium sulfate. The residue was dried in vacuo at 40° C. One obtained 0.035 g of 2-(1H-imidazol-2-yl)-4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazole (41%) as a light brown solid; M.p.: 220–224° C.

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. additionwas added
  3. extractionthe reaction mixture was extracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customThe residue was dried in vacuo at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-ad9ccba7f77e4609b3cfaa9e1bd19491
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122545B2

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