Sodium Acetate → N-{4-chloro-2-[1-(3-trifluoromethylphenoxyimino)ethyl]phenyl}trifluoromethanesulfonamide

HRID 602595Notes

Reaction equation

HRID 602595 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:31])([F:30])[C:22]1[CH:23]=[C:24]([O:28][NH2:29])[CH:25]=[CH:26][CH:27]=1.CC([O-])=O.[Na+]>CCO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[C:4]([C:1](=[N:29][O:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:31])[F:30])[CH:23]=2)[CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 21277374O-(3-trifluoromethylphenyl)hydroxylamine hydrochlorideHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 86603996N-{4-chloro-2-[1-(3-trifluoromethylphenoxyimino)ethyl]phenyl}trifluoromethanesulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (310 mg, 1.03 mmol), O-(3-trifluoromethylphenyl)hydroxylamine hydrochloride (220 mg, 1.03 mmol) and anhydrous NaOAc (93 mg, 1.13 mmol) in EtOH (18 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, 3:2). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:5) afforded N-{4-chloro-2-[1-(3-trifluoromethylphenoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 134 (430 mg, 91%), as a pale yellow solid. M.p. 63-64° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.00, br S, 1H, 7.71, d, J=9.0 Hz, 1H, 7.60, d, J=2.2 Hz, 1H, 7.56-7.35, m, 5H, 2.58, s, 3H. O-(3-Trifluoromethylphenyl)hydroxylamine hydrochloride was prepared in two steps by the procedure of Petrassi, M. H.; Sharpless, K. B.; Kelly, J. W. Org. Lett., 2001, 3, 139-142.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:5)

Sources & evidence

ORD record
ord-7d7cd2e9652a42a89746fa77bb5c1c15
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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