Hydrazine hydrate (1:1) → (Z)-[(2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydrazine

HRID 63204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63204
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:27][NH2:28]>C(Cl)Cl.C(O)C>[N:27](=[C:12](/[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)\[C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:8][CH:9]=1)\[NH2:28]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole

Produkt 1

HCID 53364199(Z)-[(2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 1h (230 mg, 0.65 mmol) in 3 mL CH2Cl2 and 3 mL ethanol was added hydrazine hydrate (2 mL). Then the mixture was refluxed for overnight. After completion of the reaction, the residue was absorbed on silica gel and purified by column chromatography to give compounds 2d-cis (80 mg) and 2d-trans (56 mg). 1H NMR (300 MHz, CDCl3) δ 8.01-7.98 (m, 2H), 7.49-7.46 (m, 5H), 7.33 (s, 1H), 6.82 (s, 2H), 3.87 (s, 3H), 3.85 (s, 6H). MS (ESI) m/z 370.1 (M+H)+.

Aufarbeitung

  1. temperatureThen the mixture was refluxed for overnight
  2. customAfter completion of the reaction
  3. customthe residue was absorbed on silica gel
  4. custompurified by column chromatography
  5. customto give compounds

Quellen und Nachweise

ORD-Eintrag
ord-e4e3ede812fd47c58e04de9c9ecb19a0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447049B2

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