Thioanisole → 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one

HRID 384489노트

반응식

HRID 384489 반응식
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:10]=1[CH3:28])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:21]([S:20][CH2:19][C:11]1[NH:12][C:13]2[C:18]([C:9](=[O:8])[C:10]=1[CH3:28])=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

4

반응물 2

HCID 7520ThioanisoleHCID 595272964-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline

생성물 1

HCID 595272552-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one수율 95.1%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 4-(benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline (150 mg) in trifluoroacetic acid (5 mL) was added thioanisole (150 mg), followed by stirring at room temperature for 16 hours. The reaction mixture was added dropwise to an ice-cold aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate (50 mL). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one (110 mg).

후처리

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

출처 및 근거

ORD 기록
ord-7d10b21b5f264ec59469e3058e13c6d9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367702B2

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