Triethylamine → HCID 178434636, Verbindung

HRID 253306

Reaktionsgleichung

Reaktionsgleichung von HRID 253306
[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]([C:15](=O)[CH3:16])[C:13]#[N:14])[CH:3]=1.Cl.Cl.[NH2:20][NH2:21].C(N(CC)CC)C>C(O)C>[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([C:12]2[C:15]([CH3:16])=[N:20][NH:21][C:13]=2[NH2:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 17548Hydrazine, dihydrochlorideHCID 668916032-(8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-3-oxobutanenitrile

Produkt 1

HCID 178434636HCID 178434636, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-3-oxobutanenitrile (0.37 g; 1.56 mmol) was dissolved in dry ethanol (5 mL) and hydrazine dihydrochloride (0.20 g, 1.87 mmol) then triethylamine (217 μg, 1.56 mmol) were added. The reaction mixture was refluxed for 2 h, cooled to rt and the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate (50 ml), washed with saturated sodium bicarbonate (2×25 mL), brine (25 ml) then dried over sodium sulfate. Filtration and concentration gave 4-(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-3-methyl-1H-pyrazol-5-amine (0.36 g, 93% yield) as an orange solid. 1H NMR (400 MHz, d6-DMSO) δ 6.75 (dd, 1H), 6.65 (m, 1H), 4.30 (m, 4H), 2.14 (s, 3H). MS (EI) for C12H12FN3O2: 250 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  4. washwashed with saturated sodium bicarbonate (2×25 mL), brine (25 ml)
  5. dry with materialthen dried over sodium sulfate
  6. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-2ab85eabb79246c9b87bc937062b31b8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872014B2

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