Sodium Acetate → N-{2-[1-(2,4-bistrifluoromethylbenzyloxyimino)ethyl]-4-chlorophenyl}trifluoromethanesulfonamide

HRID 602593Notes

Reaction equation

HRID 602593 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])(=O)[CH3:2].Cl.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:23]=1[CH2:24][O:25][NH2:26].CC([O-])=O.[Na+]>CCO>[F:20][C:21]([F:35])([F:36])[C:22]1[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[CH:27][C:23]=1[CH2:24][O:25][N:26]=[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamideHCID 86230463O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride

Product 1

HCID 86603994N-{2-[1-(2,4-bistrifluoromethylbenzyloxyimino)ethyl]-4-chlorophenyl}trifluoromethanesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (150 mg, 0.50 mmol), O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride (154 mg, 0.52 mmol) and anhydrous NaOAc (43 mg, 0.52 mmol) in EtOH (20 mL) was stirred for 15 h at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 7:3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 7.5:92.5 to 1:9) afforded a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-{2-[1-(2,4-bistrifluoromethylbenzyloxyimino)ethyl]-4-chlorophenyl}trifluoromethanesulfonamide 2 (240 mg, 89%), as a colorless oil. 1H n.m.r. (200 MHz, CDCl3) δ 10.96, br s, 1H, 7.96, s, 1H, 7.85, d, J=8.0 Hz, 1H, 7.72, d, J=8.0 Hz, 1H, 7.60, d, J=8.8 Hz, 1H, 7.49, d, J=2.2 Hz, 1H, 7.33, dd, J=2.2 and 8.8 Hz, 1H, 5.46, s, 2H, 2.39, s, 3H. HRMS (M+) 542.0102.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 7:3)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 7.5:92.5 to 1:9)
  5. customafforded a pale yellow solid which
  6. customwas recrystallized from CH2Cl2/PE

Sources & evidence

ORD record
ord-8fb4a15037d14fa7bff2ac2247bfb155
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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