Sodium Acetate → N-[2-(1-allyloxyiminoethyl)-5-trifluoromethylphenyl]trifluoromethanesulfonamide

HRID 970885Notes

Reaction equation

HRID 970885 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])(=O)[CH3:2].Cl.[CH2:23]([O:26][NH2:27])[CH:24]=[CH2:25].CC([O-])=O.[Na+]>CCO>[CH2:23]([O:26][N:27]=[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:13])[F:12])=[CH:6][C:5]=1[NH:14][S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[CH3:2])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 86604010N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide

Product 1

HCID 73038538N-[2-(1-allyloxyiminoethyl)-5-trifluoromethylphenyl]trifluoromethanesulfonamideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide 35 (168 mg, 0.50 mmol), O-allylhydroxylamine hydrochloride (60mg, 0.53 mmol) and anhydrous NaOAc (43 mg, 0.53 mmol) in EtOH (3 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, and the residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:99) to afford N-[2-(1-allyloxyiminoethyl)-5-trifluoromethylphenyl]trifluoromethanesulfonamide 241 (155 mg, 80%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.82, br s, 1H; 7.98, s, 1H; 7.65, d, J=8.2Hz, 1H; 7.49, d, J=8.2Hz, 1H; 6.02, m, 1H; 5.44, d, 3J=17.2 Hz, 1H; 5.37, d, 3J=10.4 Hz, 1H; 4.72, d, J=6.0 Hz, 2H; 2.38, s, 3H. HRMS (M+) 390.0465.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:99)

Sources & evidence

ORD record
ord-3229c286f99a4063925efc1d2de3b184
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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