Morpholine → 5-Methylsulfanyl-2-morpholin-4-yl-benzoic acid

HRID 32722

반응식

HRID 32722 반응식
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCCC.[Cu]>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

생성물 1

HCID 597935765-Methylsulfanyl-2-morpholin-4-yl-benzoic acid수율 10.1%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 62761-Pentanol용매

실험 절차

A mixture of 2-Chloro-5-(methylthio)-benzoic acid (1 g, 4.7 mmol), morpholine (620 ul, 7.1 mmol), potassium carbonate (1.05 g, 7.6 mmol) and Copper (24 mg, 0.38 mmol) in pentanol (6 ml) was stirred for 1 h at room temperature. The mixture was heated to 100° C and stirred for 40 minutes. The solvent was evaporated. The residue was taken up in water and acidified to pH 2. The aqueous layer was extracted twice with ethylacetate. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate 0-20% over 15 minutes to provide the title compound as a brown solid (120 mg, 10%), MS (m/e): 252.1 (M−H, 100%)

후처리

  1. temperatureThe mixture was heated to 100° C
  2. stirringstirred for 40 minutes
  3. customThe solvent was evaporated
  4. extractionThe aqueous layer was extracted twice with ethylacetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude oil was chromatographed over silicagel

출처 및 근거

ORD 기록
ord-e0c7711c73034553b657b8647c7d2f47
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427612B2

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