Acetic Acid → N-{4-chloro-2-[1-(2-methoxyethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide

HRID 602598Notes

Reaction equation

HRID 602598 reaction equation
CN(C)CCN.[CH3:7][O:8][CH2:9][CH2:10][O:11][N:12]1C(=O)C2=CC=CC=C2C1=O.C(O)(=O)C.[C:27]([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)[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:27](=[N:12][O:11][CH2:10][CH2:9][O:8][CH3:7])[CH3:28])[CH:35]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 129191152-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 86603999N-{4-chloro-2-[1-(2-methoxyethoxyimino)ethyl]phenyl}trifluoromethanesulfonamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N,N-Dimethylethylenediamine (2.54 mL, 22.0 mmol) was added to a solution of N-(2-methoxyethoxy)phthalimide (3.32 g, 15.0 mmol) in EtOH (50 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (20 mL) was then added to adjust the mixture to ca. pH 4, followed by the addition of a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (3.02 g, 10.0 mmol) in EtOH (2 mL), and the mixture stirred for 65 h at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:1). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 1:1) afforded N-{4-chloro-2-[1-(2-methoxyethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 185 (3.0 g, 80%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.40, br s, 1H, 7.65, d, J=8.8 Hz, 1H, 7.47, d, J=2.4 Hz, 1H; 7.33, dd, J=2.4 and 8.8 Hz, 1H, 4.37, m, 2H, 3.71, m, 2H, 3.41, s, 3H, 2.32, s, 3H. HRMS (M+) 374.0308.

Workup

  1. stirringthe mixture stirred for 65 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:1)
  4. customPurification
  5. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 1:1)

Sources & evidence

ORD record
ord-7eb85099968b4ac5ac5b76115ce72896
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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