Sodium Acetate → N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide

HRID 602614Notes

Reaction equation

HRID 602614 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][O:31][NH2:32])=[CH:28][CH:27]=1.CC([O-])=O.[Na+]>CCO>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][O:31][N:32]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 67132131O-(4-Bromobenzyl)hydroxylamine hydrochlorideHCID 67271057N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 86623961N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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 CH2Cl2/PE, 3:2). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H, 7.66, d, J=9.0 Hz, 1H, 7.55-7.48, m, 5H, 7.33-7.20, m, 5H, 6.88, d, J=2.4 Hz, 1H, 5.11, s, 2H.

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, 1:9)

Sources & evidence

ORD record
ord-23a7eab1301549b682f53f0958105d9a
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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