Diethylamine → (2-Aminothiophen-3-yl)(phenyl)methanone

HRID 51227

Reaktionsgleichung

Reaktionsgleichung von HRID 51227
[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH:13]1[CH2:18]SC(O)C[S:14]1.C(NCC)C>C(O)C>[NH2:11][C:10]1[S:14][CH:13]=[CH:18][C:9]=1[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 64799BenzoylacetonitrileHCID 983301,4-Dithiane-2,5-diol

Produkt 1

HCID 644720(2-Aminothiophen-3-yl)(phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of benzoylacetonitrile (1.45 g, 10 mmole), 2,5-dihydroxy-1,4-dithiane (0.76 g, 5 mmole) and diethylamine (0.73 g=1.04 mL, 10 mmole) in 4 mL absolute ethanol was heated in a teflon-sealed pressure tube for 4 hours at 50° C. with frequent stirring on a vortex mixer. By 2 hours starting materials had dissolved and shortly thereafter product began to crystallize. After refrigerating the tube overnight, the product was filtered off and washed with a little methanol to give bright yellow crystals. Yield 1.3 g, 64% 1H NMR (CDCl3) δ: 6.14 (d, 1H, H-5), 6.88 (d, 1H, H-4), 6.95 (br s, 2H, NH2), 7.5-7.7 (m, 5H, C6H5).

Aufarbeitung

  1. customsealed pressure tube for 4 hours at 50° C.
  2. dissolutionmaterials had dissolved
  3. customto crystallize
  4. customthe tube overnight
  5. filtrationthe product was filtered off
  6. washwashed with a little methanol
  7. customto give bright yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-8636b64787724922993be66ba485c385
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713638B2

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