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Hydrazine hydrate (1:1) → HCID 178506369, Verbindung

HRID 2053050
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2053050
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH2:15])=O.COC(OC)[N:24]([CH3:26])C.O.[NH2:30]N>C(O)(=O)C>[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]([C:13]2[N:24]=[CH:26][NH:30][N:15]=2)[CH:16]=[CH:17][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 59654362HCID 59654362, Verbindung

Produkt 1

HCID 178506369HCID 178506369, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 0.137 g (0.48 mmol) of 3-(2-trifluoromethoxyphenyl)-benzamide in 1 Ml of N,N-dimethylformamide dimethyl acetal was heated at 120° C. for 2 h at which time the reaction was concentrated in vacuo. To this material in 2.3 Ml of acetic acid was added 0.028 g (0.55 mmol) of hydrazine hydrate and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was then concentrated and partitioned between EtOAc and saturated NaHCO3 solution. The organic fraction was washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2:acetone) to give the title compound. 1H NMR (CD3OD) (δ, ppm): 8.32 (s, 1H), 8.06 (s, 1H), 7.98 (m, 1H), 7.50 (m, 3H), 7.39(m, 3H) Mass Spectrum (ESI) m/e (M+1): 306.1.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic fraction was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e903041643704d61a2a9f82e00ee3bfd
Quelldatensatz
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07326726B2

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