Acetic Acid → N-[4-chloro-2-(1-ethoxyiminobutyl)phenyl]trifluoromethanesulfonamide

HRID 970877노트

반응식

HRID 970877 반응식
CN(C)CCN.[CH2:7]([O:9][N:10]1C(=O)C2=CC=CC=C2C1=O)[CH3:8].C(O)(=O)C.[C:25]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[NH:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])(=O)[CH2:26][CH2:27][CH3:28]>CCO>[Cl:36][C:34]1[CH:33]=[CH:32][C:31]([NH:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])=[C:30]([C:25](=[N:10][O:9][CH2:7][CH3:8])[CH2:26][CH2:27][CH3:28])[CH:35]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5959292-Ethoxy-1H-isoindole-1,3(2H)-dioneHCID 67270216N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide

생성물 1

HCID 72491657N-[4-chloro-2-(1-ethoxyiminobutyl)phenyl]trifluoromethanesulfonamide수율 22%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-ethoxyphthalimide (287 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 hours. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4, followed by the addition of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide 29A (330 mg, 1.0 mmol), and the reaction stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, and the residue dissolved in Et2O (50 mL) and washed with water, brine, dried over MgSO4 and the solvent removed under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 1:1), the solvent evaporated under reduced pressure and the residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19) to afford N-[4-chloro-2-(1-ethoxyiminobutyl)phenyl]trifluoromethanesulfonamide 193 (82 mg, 22%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 12.10, br s, 1H; 7.67, d, J=8.8 Hz, 1H; 7.47, d, J=2.4 Hz, 1H; 7.32, dd, J=2.4 and 8.8 Hz, 1H; 4.27, q, J=7.2 Hz, 2H; 2.78, m, 2H; 1.59, sextet, 2H; 1.37, t, J=7.2 Hz, 3H; 1.02, t, J=7.6 Hz, 3H. HRMS (M+) 372.0514.

후처리

  1. stirringthe reaction stirred for 15 hours at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionthe residue dissolved in Et2O (50 mL)
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. filtrationThe residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 1:1)
  8. customthe solvent evaporated under reduced pressure
  9. customthe residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19)

출처 및 근거

ORD 기록
ord-59b5f7e9124f48e59f10d992ee508d83
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312248B2

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