Water → 1-[4-Phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methanamine

HRID 2194726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194726
[C:1]1([C:7]2[N:8]=[C:9]([CH2:19][N:20]3C(=O)C4C(=CC=CC=4)C3=O)[S:10][C:11]=2[S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.O>C(O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:19][NH2:20])[S:10][C:11]=2[S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 576877262-{[4-phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 576877291-[4-Phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methanamineAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 2-{[4-phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (0.53 g) in ethanol (5 mL) was added hydrazine monohydrate (0.1 mL) and the mixture was stirred at 70° C. for 1 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 0.36 g, 97%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-30e9252c8c6c4b8eb6505539f4c2bdc4
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334301B2

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