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

HRID 970855Notes

Reaction equation

HRID 970855 reaction equation
CN(C)CCN.[CH:7]1([O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.C(O)(=O)C.[C:28]([C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1[NH:38][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40])(=O)[CH3:29]>CCO>[Cl:37][C:35]1[CH:34]=[CH:33][C:32]([NH:38][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40])=[C:31]([C:28](=[N:13][O:12][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH3:29])[CH:36]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 86603998N-[4-chloro-2-(1-cyclopentyloxyiminoethyl)phenyl]trifluoromethanesulfonamideYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(cyclopentyloxy)phthalimide (345 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (302 mg, 1.0 mmol) in EtOH (2 mL), and the reaction stirred for 2.25 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19) to afford N-[4-chloro-2-(1-cyclopentyloxyiminoethyl)phenyl]trifluoromethanesulfonamide 163 (185 mg, 48%), as a pale yellow solid. 1H n.m.r. (400 MHz, CDCl3) δ 12.18, br s, 1H; 7.67, d, J=8.8 Hz, 1H; 7.49, d, J=2.4 Hz, 1H; 7.31, dd, J=2.4 and 8.8 Hz, 1H; 4.80, m, 1H; 2.30, s, 3H; 1.89, m, 4H; 1.74, m, 2H; 1.64, m, 2H. HRMS (M+) 384.0518.

Workup

  1. stirringthe reaction stirred for 2.25 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19)

Sources & evidence

ORD record
ord-81b927e4f0c54253a3953dc66bb2e759
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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