Triethylamine → HCID 22473796, Verbindung

HRID 2183662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183662
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:14]2[S:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1.Cl.[CH3:22][NH:23][O:24][CH3:25].C(N(CC)CC)C>ClCCl.CN(C)C=O.O>[CH3:25][O:24][N:23]([CH3:22])[C:18]([C:16]1[S:15][C:14]2[C:9]([O:8][CH3:7])=[CH:10][CH:11]=[CH:12][C:13]=2[CH:17]=1)=[O:20]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 8217517-Methoxybenzo[b]thiophene-2-carboxylic acid

Produkt 1

HCID 22473796HCID 22473796, VerbindungAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (1 ml) was added dropwise under nitrogen at 0° C. to a stirred suspension of 7-methoxybenzo[b]thiophene-2-carboxylic acid (1.9 g) in dichloromethane (25 ml), then dimethylformamide (2 drops) was added and the mixture was stirred at ambient temperature for 4.5 hours. N,O-Dimethylhydroxylamine hydrochloride (1 g), triethylamine (3.2 ml) and dichloromethane (5 ml) were added, the mixture was stirred at ambient temperature for 19 hours, then it was poured into water (60 ml). The product was extracted into dichloromethane (2×30 ml), the combined extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using dichloromethane as eluant. Appropriate fractions were combined and the solvent removed in vacuo to give N,7-dimethoxy-N-methylbenzo[b]thiophene-2-carboxamide (1.5 g) as a gum which was used without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 19 hours
  2. extractionThe product was extracted into dichloromethane (2×30 ml)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by flash chromatography over silica
  6. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-994ba68bfc764de09258bba7995f7c39
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900216B2

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