2-Thiophenecarboxylic acid → HCID 47222443, Verbindung

HRID 397049

Reaktionsgleichung

Reaktionsgleichung von HRID 397049
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=[O:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N(CC)CCCN=C=NCC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:17]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 107002-Thiophenecarboxylic acidHCID 748663-MethoxyphenethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Produkt 1

HCID 47222443HCID 47222443, VerbindungAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 3-methoxyphenethylamine (1.000 g, 6.61 mmol), 2-thiophenecarboxylic acid (0.847 g, 6.61 mmol), 1-hydroxybenzotriazole hydrate (1.340 g, 9.92 mmol), and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.330 g, 6.94 mmol) in anhydrous CH2Cl2 (20 ml) was stirred at 0° C. under N2 for 1 hr, then warmed to rt and stirred at rt for 18 hr. The reaction mixture was washed with 1M NaOH (10 ml) followed by 1M HCl (10 ml), dried over MgSO4, and concentrated in vacuo to give 1.859 g of yellow oil. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 1.637 g (95% yield) of yellow oil.

Aufarbeitung

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 18 hr
  3. washThe reaction mixture was washed with 1M NaOH (10 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-383e5819d9164389b3de5122ca6e2c14
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608203B2

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