Acetic Acid → N-{4-chloro-[(2-methoxyethoxyimino)phenylmethyl]phenyl}trifluoromethanesulfonamide

HRID 602616ノート

反応式

HRID 602616 の反応式
CN(C)CCN.[CH3:7][O:8][CH2:9][CH2:10][O:11][N:12]1[C:16](=O)[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2C1=O.C(O)(=O)C.C([C:35]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:36]=1[NH:42][S:43]([C:46]([F:49])([F:48])[F:47])(=[O:45])=[O:44])(=O)C1C=CC=CC=1>CCO>[Cl:41][C:39]1[CH:40]=[CH:35][C:36]([NH:42][S:43]([C:46]([F:49])([F:47])[F:48])(=[O:45])=[O:44])=[C:37]([C:16](=[N:12][O:11][CH2:10][CH2:9][O:8][CH3:7])[C:15]2[CH:14]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:38]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 129191152-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67271057N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide

生成物 1

HCID 72491806N-{4-chloro-[(2-methoxyethoxyimino)phenylmethyl]phenyl}trifluoromethanesulfonamide収率 74.2%

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-(2-methoxyethoxy)phthalimide (332 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 7 hours. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4, followed by the addition of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (364 mg, 1.0 mmol), and the reaction stirred for 15 hours at 30° C. 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 purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19) to afford N-{4-chloro-[(2-methoxyethoxyimino)phenylmethyl]phenyl}trifluoromethanesulfonamide 234 (324 mg, 74%), as a colorless oil, 1H n.m.r. (400 MHz, CDCl3) (2:1 mixture of E- and Z-isomers) δ 11.06, br s, 1H, 8.87, br s, 1H, 7.67, d, J=88 Hz, 1H, 7.54-7.31, m, 13H, 7.10, d, J=2.4 Hz, 1H; 6.92, d, J=2.4 Hz, 1H, 4.33, m, 4H, 3.67, m, 4H, 3.46, s, 3H, 3.38, s, 3H. HRMS (M+) 436.0465.

後処理

  1. stirringthe reaction stirred for 15 hours at 30° C
  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. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19)

出典と根拠

ORDレコード
ord-54841250efa247f38518ee965a0af872
出典データセット
uspto-grants-2011_03
特許番号
US07906538B2

反応ノート

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