3,5-Di-tert-butyl-4-hydroxybenzoic acid → 4-[3-(3,5-Di-t-butyl-4-hydroxybenzoylamino)propylthio]pyridine

HRID 6111

Reaktionsgleichung

Reaktionsgleichung von HRID 6111
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.[NH2:39][CH2:40][CH2:41][CH2:42][S:43][C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:13]=1[OH:14])[C:8]([NH:39][CH2:40][CH2:41][CH2:42][S:43][C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1)=[O:9])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 152276954-(3-Aminopropylthio)pyridine

Produkt 1

HCID 190791594-[3-(3,5-Di-t-butyl-4-hydroxybenzoylamino)propylthio]pyridineAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.49 g (5.94 mmol) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 889 mg (7.73 mmol) of N-hydroxysuccinimide in 60 ml of methylene chloride was added 1.38 g (7.13 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. Further 1.00 g (5.94 mmol) of 4-(3-aminopropylthio)pyridine was added and the mixture was stirred at rcom temperature for 8 hours. The reaction mixture was washed with water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 650 mg of the desired compound (27.3%, colorless powder), mp: 203.0°-204.0° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringthe mixture was stirred at rcom temperature for 8 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: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2c8dc63242cc44cab385e6bb518c6cff
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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