Lawesson's reagent → (R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1lambda6-thiomorpholin-3-thione

HRID 920165노트

반응식

HRID 920165 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]2([CH3:19])[NH:13][C:12](=O)[C:11]([CH3:16])([CH3:15])[S:10](=[O:18])(=[O:17])[CH2:9]2)[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]2([CH3:19])[NH:13][C:12](=[S:30])[C:11]([CH3:16])([CH3:15])[S:10](=[O:18])(=[O:17])[CH2:9]2)[CH:7]=1

참가 물질

5

반응물 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 90016634(R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1lambda6-thiomorpholin-3-one

생성물 1

HCID 90067099(R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1lambda6-thiomorpholin-3-thione수율 89.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

To a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1λ6-thiomorpholin-3-one (1.4 g, 3.84 mmol, Eq: 1.00) in dioxane (29.5 ml) was added Lawesson's reagent (3.10 g, 7.68 mmol, Eq: 2.00). The reaction mixture was stirred at 80° C. for 10 hours. The reaction mixture was poured into sat. NaHCO3-solution and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give a light yellow oil. The residue was chromatographed on 20 g silica gel with ethyl acetate in heptane to give (R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1λ6-thiomorpholin-3-thione (1.3 g, 3.42 mmol, 88.9% yield) as a light yellow foam. MS (ISP): m/z=380.0 [M+H]+ and 382.3 [M+2+H]+.

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a light yellow oil
  7. customThe residue was chromatographed on 20 g silica gel with ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-b3f28cc96ce04b269310e22afbc2bc26
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273042B2

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