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

HRID 970873Notes

Reaction equation

HRID 970873 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-b33fddbae8754ee28a314194b70557b5
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

Loading…