Acetyl chloride → N-acetyl-N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide

HRID 602626Notes

Reaction equation

HRID 602626 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](=[N:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:17][CH3:18])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:35](Cl)(=[O:37])[CH3:36]>CC(C)=O>[C:35]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:16](=[N:19][O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[CH2:17][CH3:18])[S:9]([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:11])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 86604011N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide2×

Product 1

HCID 76839251N-acetyl-N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide (compound 11) (150 mg, 0.33 mmol) and K2CO3 (137 mg, 0.99 mmol) in acetone (5 mL) was added acetyl chloride (70 μL, 0.99 mmol), and the reaction allowed to stir at RT for 2 hours. The reaction mixture was concentrated under vacuum and the residue dissolved in CHCl3 (20 mL), washed with H2O (15 mL) dried over MgSO4 and concentrated under reduced pressure. The residue was purified by radial thin layer chromatography (eluting with EtOAc/PE, 1:19) to afford N-acetyl-N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide 307 (156 mg, 95%), as a pale yellow solid. M.p. 64-66° C. 1H n.m.r. (400 MHz, CDCl3) δ 7.51, d, J=2.4 Hz, 1H; 7.42, dd, J=2.4 and 8.8 Hz, 1H, 7.30, m, 4H, 7.23, d, J=2.4 Hz, 1H, 5.12, m, 2H, 2.83, m, 1H, 2.67, m, 1H, 1.91, s, 3H, 1.18, t, J=7.6 Hz, 3H.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue dissolved in CHCl3 (20 mL)
  3. washwashed with H2O (15 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by radial thin layer chromatography (eluting with EtOAc/PE, 1:19)

Sources & evidence

ORD record
ord-4d931845bee84f9b83716daac8e8351b
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

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