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

HRID 602621Notes

Reaction equation

HRID 602621 reaction equation
CN(C)CCN.[CH:7]([O:10][N:11]1[C:15](=O)[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2C1=O)([CH3:9])[CH3:8].C(O)(=O)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:29](C(C2CCCCC2)=O)[CH:28]=1>CCO>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([NH:33][S:34]([C:37]([F:40])([F:38])[F:39])(=[O:36])=[O:35])=[C:31]([C:15]([CH:14]2[CH2:13][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:11][O:10][CH:7]([CH3:8])[CH3:9])[CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 27689132-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67270465N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide

Product 1

HCID 72491797N-[4-chloro-2-(cyclohexylisopropoxyiminomethyl)phenyl]trifluoromethanesulfonamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-isopropoxyphthalimide (308 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-(4-chloro-2-cyclohexanecarbonylphenyl)-trifluoromethanesulfonamide 29E (370 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 purified by column chromatography (eluting with CH2Cl2/PE, 1:1) to afford N-[4-chloro-2-(cyclohexylisopropoxyiminomethyl)phenyl]trifluoromethanesulfonamide 210 (390 mg, 91%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) (1:1 mixture of E- and Z-isomers) δ 10.59, br s, 1H; 8.11, br s, 1H, 7.61, d, J=8.8 Hz, 1H, 7.49, d, J=8.8 Hz, 1H, 7.46, d, J=2.4 Hz, 1H, 7.42, dd, J=2.4 and 8.8 Hz, 1H, 7.30, dd, J=2.4 and 8.8 Hz, 1H, 7.24, d, J=2.4 Hz, 1H, 4.49, m, 1H, 4.39, m, 1H, 2.97, m, 1H, 2.45, m, 1H, 1.97-1.71, m, 14H, 1.34-1.24, m, 18H. HRMS (M+) 426.0983.

Workup

  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. customThe residue was purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

Sources & evidence

ORD record
ord-a696e74a30824dcaaa7c2f046e8ba9a5
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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