Sodium Acetate → HCID 86604004, compound

HRID 970865Notes

Reaction equation

HRID 970865 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.[CH2:21]([O:24][NH2:25])[CH:22]=[CH2:23].CC([O-])=O.[Na+]>CCO>[CH2:21]([O:24][N:25]=[C:16]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH2:17][CH3:18])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

Product 1

HCID 86604004HCID 86604004, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol), O-allylhydroxylamine hydrochloride (119 mg, 1.05 mmol) and anhydrous NaOAc (86 mg, 1.05 mmol) in EtOH (5 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 EtOAc/PE, 1:9). The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:99 to 1:19) to afford N-[2-(1-allyloxyiminopropyl)-4-chlorophenyl]trifluoromethanesulfonamide 156 (116 mg, 31%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.57, br s, 1H; 7.67, d, J=8.8 Hz, 1H; 7.48, d, J=2.4 Hz, 1H; 7.33, dd, J=2.4 and 8.8 Hz, 1H; 6.00, m, 1H; 5.42, d, 3J=17.2 Hz, 1H; 5.36, d, 3J=10.4 Hz, 1H; 4.68, d, J=6.0 Hz, 2H; 2.83, q, J=7.6 Hz, 2H; 1.19, t, J=7.6 Hz, 3H. HRMS (M+) 370.0350.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with EtOAc/PE, 1:9)
  3. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:99 to 1:19)

Sources & evidence

ORD record
ord-0ea3c317d8a24db8931b0118a5582fbf
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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