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

HRID 602616Notes

Reaction equation

HRID 602616 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-54841250efa247f38518ee965a0af872
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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