Sodium Acetate → HCID 86604004, compound

HRID 602607Notes

Reaction equation

HRID 602607 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)trifluorcmethanesulfonamide 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-70c268dfd4134c49a62a0f13ff6efc50
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

Loading…