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

HRID 970877ノート

反応式

HRID 970877 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-59b5f7e9124f48e59f10d992ee508d83
出典データセット
uspto-grants-2007_12
特許番号
US07312248B2

反応ノート

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