Triethylamine → alpha-(3-Trifluoromethylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850259Notes

Reaction equation

HRID 850259 reaction equation
[OH:1][N:2]=[C:3]([C:14]#[N:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>C(#N)C>[F:29][C:17]([F:16])([F:28])[C:18]1[CH:19]=[C:20]([S:24]([O:1][N:2]=[C:3]([C:14]#[N:15])[C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=2)(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 53895123alpha-(3-Trifluoromethylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As described under 1.2., 4.1 g (0.02 mol) of a-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 5.4 g (0.022 mol) of 3-trifluoromethylphenylsulfonic acid chloride in the presence of triethylamine. After recrystallisation of the crude product from ethyl acetate/-hexane, 6.6 g (80%) of α-(3-trifluoromethyl-phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of yellowish crystals having a melting point of 129-130° C. The 1H-NMR spectrum of the compound shows that it is a pure stereoisomer. The UV spectrum (acetonitrile) of the substance shows a broad absorption band with a maximum at 351 nm (ε=11700) that extends to 430 nm. Elemental analysis: C17H13F3N2O5S (414.36)

Workup

  1. customAfter recrystallisation of the crude product from ethyl acetate/-hexane, 6.6 g (80%) of α-(3-trifluoromethyl-phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide
  2. customare obtained in the form of yellowish crystals

Sources & evidence

ORD record
ord-361eb1000f614b87a369a8e56a5221ce
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

Loading…