Thiophene-3-carboxylic acid → 4-[3-(3-Thiophenecarbonylamino)propylthio]pyridine

HRID 6121

Reaktionsgleichung

Reaktionsgleichung von HRID 6121
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.[NH2:29][CH2:30][CH2:31][CH2:32][S:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:29][CH2:30][CH2:31][CH2:32][S:33][C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[O:8])=[CH:2]1

Komponenten

6

Edukt 4

HCID 6918Thiophene-3-carboxylic acidHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 152276954-(3-Aminopropylthio)pyridine

Produkt 1

HCID 190790934-[3-(3-Thiophenecarbonylamino)propylthio]pyridineAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g (7.80 mmol) of thiophene-3-carboxylic acid and 1.08 g (10.1 mmol) of N-hydroxysuccinimide in 70 ml of methylene chloride, 1.80 g (9.36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1 hour. Further, 1.31 g (7.80 mmol) of 4-(3-aminopropylthio)pyridine was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10) to obtain 1.65 g of the desired compound (yield: 76.1%, colorless powder).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. washThe reaction mixture was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-98480977321a48fc9c80434e5c786ddb
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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