Tetrahydrofuran → 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide

HRID 22884

Reaktionsgleichung

Reaktionsgleichung von HRID 22884
C(N(CC)CC)C.C1COCC1.[NH2:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21].[Br:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>O>[Br:25][CH2:26][CH2:27][CH2:28][C:29]([NH:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21])=[O:30]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

Produkt 1

HCID 225921434-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Triethylamine (206 mg, 2.04 mmol) was added to a THF (6 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (341 mg, 1.70 mmol), and 4-bromobutanoyl chloride (379 mg, 2.04 mmol) was then slowly added thereto dropwise while being cooled with ice. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent-hexane:acetone=5:1→3:1) to obtain 390 mg (yield 66%) of 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide as a colorless crystal (melting point: 139 to 140° C.).

Aufarbeitung

  1. additionwas then slowly added
  2. temperaturedropwise while being cooled with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent-hexane:acetone=5:1→3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c12b1eb5f9fa48d18395bc047a0571bf
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849647B1

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