Dimethyl Sulfoxide → HCID 11516373, 화합물

HRID 1987224

반응식

HRID 1987224 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1.CS(C)=O.C(CN)O>O>[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH2:20][CH2:19]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 3286362N-(4-fluoro-3-nitrophenyl)ethanesulfonamide2회HCID 156044941-(4,4-Difluorocyclohexyl)methanamine

생성물 1

HCID 11516373HCID 11516373, 화합물수율 63.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

N-(4-Fluoro-3-nitrophenyl)ethanesulfonamide (26 g, 0.107 mol), [(4,4-difluorocyclohexyl)methyl]amine (approx. 15 g), DIPFA (20 mL) and DMSO (100 mL) were mixed together and heated to 65° C. overnight. Ethanolamine (5 g) was added and the reaction mixture was stirred until complete disappearance of N-(4-fluoro-3-nitrophenyl)ethanesulfonamide (approx. 4-5 hrs.). The room temperature cooled down reaction mixture was poured in cold water (900 mL). The product was extracted with DCM (5×200 mL). The combined organic phases were washed with HCl 2N (3×200 mL) and dried over anhydrous Na2SO4. The solvent was removed and the crude product was purified on silica gel by flash chromatography (this material can be re-crystallized using a mixture of EtOAc and hexane) to provide the title product (24.2 g) as orange solid.

후처리

  1. temperatureThe room temperature cooled down
  2. customreaction mixture
  3. extractionThe product was extracted with DCM (5×200 mL)
  4. washThe combined organic phases were washed with HCl 2N (3×200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed
  7. customthe crude product was purified on silica gel by flash chromatography (this material
  8. customcan be re-crystallized
  9. additiona mixture of EtOAc and hexane)

출처 및 근거

ORD 기록
ord-98c8825b80c04d309453a53714842663
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550495B2

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