Acetic Acid → N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamide

HRID 970867Notes

Reaction equation

HRID 970867 reaction equation
CN(C)CCN.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][O:13][N:14]1C(=O)C2=CC=CC=C2C1=O.C(O)(=O)C.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38])=[C:32]([C:44](=O)[CH2:45][CH3:46])[CH:31]=1>CCO>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38])=[C:32]([C:44](=[N:14][O:13][CH2:12][C:8]2[S:7][CH:11]=[CH:10][CH:9]=2)[CH2:45][CH3:46])[CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 107064032-(2-Thienylmethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

Product 1

HCID 86604005N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(thiophen-2-ylmethoxy)phthalimide (365 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (1 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 15 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1) to afford N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamide 207 (364 mg, 85%), as a white solid. M.p. 53-54° C. 1H n.m.r. (400 MHz, CDCl3) δ 11.49, br s,1H; 7.64, d, J=8.8 Hz, 1H; 7.47, d, J=2.4 Hz, 1H; 7.33, m, 2H; 7.16, m, 1H; 7.01, m, 1H; 2.82, q, J=7.6 Hz, 2H; 1.17, t, J=7.6 Hz, 3H. HRMS (M+) 426.0065.

Workup

  1. stirringthe mixture stirred for 15 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

Sources & evidence

ORD record
ord-f98add91de98481fb39c23f23117a673
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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