3-(Phenylthio)-2-propenoic acid → HCID 68488496, Verbindung

HRID 1882338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882338
[C:1]1([S:7][CH:8]=[CH:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:18][C:17]([S:19][CH3:20])=[N:16][CH:15]=1>C(#N)C.C(N(CC)CC)C>[CH3:20][S:19][C:17]1[S:18][C:14]([NH:13][C:10](=[O:12])[CH:9]=[CH:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][N:16]=1

Komponenten

5

Edukt 2

HCID 2757063-(Phenylthio)-2-propenoic acidHCID 132489052-(Methylsulfanyl)-1,3-thiazol-5-amine

Produkt 1

HCID 68488496HCID 68488496, VerbindungAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 3-(phenylthio)acrylic acid (3.69 g) in acetonitrile (50 mL) were added a solution of 5-amino-2-(methylthio)thiazole (3.00 g) in acetonitrile (10 mL) and triethylamine (2.80 mL) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and then at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 mL), which was extracted with ethyl acetate (100 mL) twice. The organic layers were combined, washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain N-[2-(methylthio)thiazol-5-yl]-3-(phenylthio)acrylamide (1.90 g) as a dark yellow crystal.

Aufarbeitung

  1. temperaturecooling
  2. waitat room temperature for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added 1N hydrochloric acid (50 mL), which
  5. extractionwas extracted with ethyl acetate (100 mL) twice
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9eecd080a22147d9806460c5a3f6c1f6
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318981B2

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