Morpholine → 3-(Morpholinosulfonyl)pyridine

HRID 489901

Reaktionsgleichung

Reaktionsgleichung von HRID 489901
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([OH:16])(=[O:15])=[O:14])[CH:8]=1.C(N(CC)CC)C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+]>CO.C1(C)C=CC=CC=1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([Cl:2])(=[O:16])=[O:14])[CH:8]=1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)(=[O:15])=[O:16])[CH:8]=1

Komponenten

9

Edukt 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Produkt 2

HCID 3164136Pyridine-3-sulfonyl chlorideHCID 42764363-(Morpholinosulfonyl)pyridineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Pyridine-3-sulfonyl chloride was prepared from phosphorus pentachloride (17.82 g, 0.112 mol) and pyridine-3-sulfonic acid (12.36 g, 77.7 mmol) according to the procedure described by P. Breant et al. Synthesis, 1983, 822. Anhydrous toluene (20 mL) was added to the product and this solution added slowly to a mixture of toluene (100 mL), triethylamine (4 eq, 43 mL) and morpholine (1.5 eq, 10.3 mL) with cooling in ice water. A thick precipitate was formed. The mixture was stirred for 16 hr and then shaken with a saturated K2CO3 solution, dried over anhydrous sodium sulfate and evaporated to give a yellowish brown solid. Trituration with methanol gave 4-(pyridine-3-sulfonyl)-morpholine as a pale yellow solid (14.29 g, 81%).

Aufarbeitung

  1. customBreant et al. Synthesis, 1983, 822
  2. customA thick precipitate was formed
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give a yellowish brown solid

Quellen und Nachweise

ORD-Eintrag
ord-bc41d7d1737f4fca93c428f6248810d9
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979741B2

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