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

HRID 602611Notes

Reaction equation

HRID 602611 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]([CH:16]=O)[CH:3]=1.Cl.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][NH2:25].CC([O-])=O.[Na+]>CCO>[F:19][C:20]([F:34])([F:35])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][N:25]=[CH:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 86230463O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochlorideHCID 86230476N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide

Product 1

HCID 86604006N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide 24 (180 mg, 0.63 mmol), O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride (342 mg, 1.16 mmol) and anhydrous NaOAc (141 mg, 1.72 mmol) in EtOH (10 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CHCl3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 3:7) afforded N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide 65 (192 mg, 58%), as a yellow solid. M.p. 65-67° C. 1H n.m.r. (200 MHz, CDCl3) δ 10.38, br s, 1H, 8.20, s, 1H, 7.97, s, 1H, 7.86, d, J=8.0 Hz, 1H, 7.75, d, J=8.0 Hz, 1H; 7.65, d, J=8.8 Hz, 1H, 7.35, dd, J=2.4 and 8.8 Hz, 1H, 7.28, d, J=2.4 Hz, 1H, 5.44, s, 2H.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CHCl3)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 3:7)

Sources & evidence

ORD record
ord-5ab1cdd27a154dd8a2578928cea44582
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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