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

HRID 602625Notes

Reaction equation

HRID 602625 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 (60 mg, 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=8.2 Hz, 1H; 7.49, d, J=8.2 Hz, 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-3105d1e7be134887a75b18d8259ce8b0
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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