Sodium Acetate → HCID 86623962, compound

HRID 970882Notes

Reaction equation

HRID 970882 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)[CH:17]([CH3:19])[CH3:18])[CH:3]=1.Cl.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][NH2:30])=[CH:25][CH:24]=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:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[CH:17]([CH3:19])[CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 20445467O-(4-chlorophenyl)hydroxylamine hydrochlorideHCID 67271504HCID 67271504, compound

Product 1

HCID 86623962HCID 86623962, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-isobutyrylphenyl)trifluoromethanesulfonamide 31B (244 mg, 1.11 mmol), O-(4-Chlorophenyl)hydroxylamine hydrochloride (200 mg, 0.91 mmol) and anhydrous NaOAc (91 mg, 1.11 mmol) in EtOH (10 mL) was stirred for 48 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7) to afford N-{4-chloro-2-[1-(4-chlorophenoxyimino)-2-methylpropyl]phenyl}trifluoromethanesulfonamide 215 (80 mg, 24%), as an orange oil. 1H n.m.r. (200 MHz, CDCl3) δ 7.56, d, J=8.8 Hz, 1H; 7.45, dd, J=2.4 and 8.8 Hz, 1H; 7.27, d, J=9.0 Hz, 2H; 7.23, d, J=2.4 Hz, 1H; 7.07, d, J=9.0 Hz, 2H; 2.94, m,1H; 1.37, s, 3H; 1.19, s, 3H.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7)

Sources & evidence

ORD record
ord-465e725672084466ac563e64054b434a
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

Loading…