Triethylamine → N-(6-acetyl-1,3-benzodioxol-5-yl)-1-benzofuran-3-carboxamide

HRID 38651

Reaktionsgleichung

Reaktionsgleichung von HRID 38651
[O:1]1[CH:5]=[C:4]([C:6](Cl)=[O:7])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.C(N(CC)CC)C.[CH3:20][C:21]([C:23]1[C:28]([NH2:29])=[CH:27][C:26]2[O:30][CH2:31][O:32][C:25]=2[CH:24]=1)=[O:22]>C1(C)C=CC=CC=1>[C:21]([C:23]1[C:28]([NH:29][C:6]([C:4]2[C:3]3[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=3[O:1][CH:5]=2)=[O:7])=[CH:27][C:26]2[O:30][CH2:31][O:32][C:25]=2[CH:24]=1)(=[O:22])[CH3:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1200001-(6-Amino-1,3-benzodioxol-5-yl)ethan-1-oneHCID 130247201-Benzofuran-3-carbonyl chloride

Produkt 1

HCID 44220313N-(6-acetyl-1,3-benzodioxol-5-yl)-1-benzofuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Into solutions of 154 (5.0 mmol) in 200 mL of dry toluene were added triethylamine (4 mL) and 2-amino-4,5-methylenedioxy acetophenone (148) (5 mmol). The mixtures were stirred at 20±2° C. for 24 h and then evaporated. The residues were washed with acetone and EtOH and then recrystallized from acetone or EtOH to form 155. Obtained as a pale-yellow solid; mp 144-145° C.; ESI-MS (Positive mode): m/z 324 [M+H]+; 1H-NMR (400 MHz, DMSO-d6): δ 2.63 (3H, s), 6.19 (2H, s), 7.41-7.50 (21-1, m), 7.68 (1H, s), 7.75 (1H, dd, J=1.6, 6.8 Hz), 8.15 (1H, dd, J=2.0, 8.8 Hz), 8.27 (1H, s), 8.71 (1H, s), 12.63 (1H, s); IR (KBr): 1635, 1677 (C═O) cm−1.

Aufarbeitung

  1. customevaporated
  2. washThe residues were washed with acetone and EtOH
  3. customrecrystallized from acetone or EtOH

Quellen und Nachweise

ORD-Eintrag
ord-f9b04acd88cd445f8767056ebf37512a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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