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

HRID 602601Notes

Reaction equation

HRID 602601 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16](=O)[CH2:17][CH3:18])[CH:3]=1.Cl.[F:21][C:22]([F:37])([F:36])[C:23]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:24]=1[CH2:25][O:26][NH2:27].CC([O-])=O.[Na+]>CCO>[F:21][C:22]([F:36])([F:37])[C:23]1[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=[CH:28][C:24]=1[CH2:25][O:26][N:27]=[C:16]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamideHCID 86230463O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride

Product 1

HCID 73005516N-{2-[1-(2,4-bistrifluoromethylbenzyloxyimino)propyl]-4-chlorophenyl}trifluoromethanesulfonamideYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (3.21 mg, 10.17 mmol), O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride (3.16 mg, 10.68 mmol) and anhydrous NaOAc (876 mg, 10.68 mmol) in EtOH (120 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, 2:3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded a pale yellow solid which was recrystallized from CH2Cl2PE to give N-{2-[1-(2,4-bistrifluoromethylbenzyloxyimino)propyl]-4-chlorophenyl}trifluoromethanesulfonamide 76 (3.70 g, 65%), as a pale yellow oil. 1H n.m.r. (200 MHz, CDCl3) δ 10.96, br s, 1H; 7.96, s, 1H, 7.85+d, J=8.4 Hz, 1H, 7.72, d, J=8.4 Hz, 1H, 7.61, d, J=8.8 Hz, 1H, 7.49, d, J=2.4 Hz, 1H, 7.33, dd, J=2.4 and 8.8 Hz, 1H, 5.45, s, 2H, 2.88, q, J=7.6 Hz, 2H, 1.21, t, J=7.6 Hz, 3H. HRMS (M+) 556.0254.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 2:3)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9)
  5. customafforded a pale yellow solid which
  6. customwas recrystallized from CH2Cl2PE

Sources & evidence

ORD record
ord-28b6e66bf27f42b984f7860c1a25c92e
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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