Morpholine → 3-(Morpholinosulfonyl)pyridine

HRID 489901

반응식

HRID 489901 반응식
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

참가 물질

9

반응물 5

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

생성물 2

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bc41d7d1737f4fca93c428f6248810d9
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06979741B2

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