Ethanolamine → HCID 59596532, Verbindung

HRID 2264913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264913
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.CO>C(O)(C)C>[OH:2][CH2:1][CH2:3][NH:4][C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 700EthanolamineHCID 887MethanolHCID 81531DiisopropylethylamineHCID 134111124-Chloro-nicotinonitrile

Produkt 1

HCID 59596532HCID 59596532, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of ethanolamine (0.60 mL, 10.0 mmol), 4-chloronicotinonitrile (1.38 g, 10.0 mmol) and diisopropylethylamine (1.74 mL, 10.0 mmol) in isopropanol was heated at reflux for 2.5 hours. It was cooled to room temperature and loaded on to a 50 g SCX-2 cartridge preconditioned with methanol. The cartridge was eluted with methanol and then with a 2M solution of ammonia in methanol. Collecting appropriate fractions followed by evaporation of solvents gave the title compound as a beige solid (1.20 g, 74%). 1H NMR (d6-DMSO, 400 MHz) 8.40 (s, 1H), 8.21 (d, J=6.3 Hz, 1H), 6.94 (bs, 1H), 6.77 (d, J=6.3 Hz, 1H), 4.84 (bs, 1H), 3.55 (t, J=6.0 Hz, 2H), 3.31 (dt, J=6.0 Hz, 6.0 Hz, 2H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. washThe cartridge was eluted with methanol
  4. customCollecting appropriate fractions
  5. customfollowed by evaporation of solvents

Quellen und Nachweise

ORD-Eintrag
ord-286e4b3630f34b8a96c972b56a27b03e
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855216B2

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