p-Toluenesulfonic acid → 4-(1,3-Thiazol-2-yl)phenol

HRID 56084

Reaktionsgleichung

Reaktionsgleichung von HRID 56084
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[S:8])[NH2:7])=[CH:4][CH:3]=1.Br[CH2:12][CH:13](OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:8][CH:12]=[CH:13][N:7]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 27593444-Hydroxythiobenzamide

Produkt 1

HCID 2238404-(1,3-Thiazol-2-yl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90° C. for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H2O (200 mL), adjusted to pH 10 with saturated NaHCO3 aqueous solution and extracted with DCM (200 mL×3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 90° C. for 24 h
  2. temperaturecooled to rt
  3. concentrationconcentrated in vacuo
  4. additionThe mixture was diluted with H2O (200 mL)
  5. extractionextracted with DCM (200 mL×3)
  6. concentrationThe combined organic phases were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-18f547aa7dbd4e959f7a411db9b1cb6c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

Verknüpfte Notizen

Wird geladen…