Morpholine → 4-((4-(Bromomethyl)phenyl)sulfonyl)morpholine

HRID 244270노트

반응식

HRID 244270 반응식
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(OCC)C.O>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

생성물 1

HCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholine수율 71%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+.

후처리

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customSolvents were removed
  6. customto yield an orange oil, which
  7. customwas purified on a 40 g silica gel column

출처 및 근거

ORD 기록
ord-13b4849bbc1a40dda980430c6255df12
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658129B2

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