Hydroxylamine, O-((4-chlorophenyl)methyl)-, hydrochloride (1:1) → N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide

HRID 602602Notes

Reaction equation

HRID 602602 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.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][O:27][NH2:28])=[CH:24][CH:23]=1.CC([O-])=O.[Na+]>CCO>[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](=[N:28][O:27][CH2:26][C:25]2[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=2)[CH2:17][CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 217573Hydroxylamine, O-((4-chlorophenyl)methyl)-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

Product 1

HCID 86604011N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamideYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (1.75 g, 5.54 mmol), O-(4-chlorobenzyl)hydroxylamine hydrochloride (1.13 g, 5.82 mmol) and anhydrous NaOAc (477 mg, 5.82 mmol) in EtOH (80 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, 1:9) afforded a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide 11 (1.74 mg, 69%), as a white solid. M.p. 54-55° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.55, br s, 1H, 7.63, d, J=8.8 Hz, 1H, 7.47, d, J=2.2 Hz, 1H, 7.39-7.29, m, 5H; 5.17, s, 2H, 2.84, q, J=7.6 Hz, 2H, 1.18, t, J=7.6 Hz, 3H.

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)
  5. customafforded a pale yellow solid which
  6. customwas recrystallized from CH2Cl2/PE

Sources & evidence

ORD record
ord-549afe27ee134e0895b559d838fb6d02
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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