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

HRID 602597Notes

Reaction equation

HRID 602597 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. N-(Cyclopentyloxy)phthalimide was prepared by the procedure of Ishikawa, T.; Kamiyama, K.; Matsunaga, N.; Tawada, H.; lizawa, Y.; Okonogi, K.; Miyake, A. J. Antibiot., 2000, 53, 1071-1085.

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-1b4fe97f03cc40288157e766ec127a10
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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