4-Methoxybenzenesulfonyl chloride → alpha-(4-Methoxyphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850260Notes

Reaction equation

HRID 850260 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.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([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:26])=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 54201532alpha-(4-Methoxyphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As described under 1.2., 10.3 g (0.05 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 11.37 g (0.055 mol) of 4-methoxyphenylsulfonic acid chloride in the presence of 7.6 g of triethylamine. After recrystallisation of the crude product from ethyl acetate/hexane, 3.26 g (17%) of α-(4-methoxy-phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of yellowish crystals having a melting point of 161-167° 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 349 nm (ε=11700) that extends to 435 nm. Elemental analysis: C17H16N2O6S (376.38)

Workup

  1. customAfter recrystallisation of the crude product from ethyl acetate/hexane, 3.26 g (17%) of α-(4-methoxy-phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide
  2. customare obtained in the form of yellowish crystals

Sources & evidence

ORD record
ord-ddf5cd72853945c09f29acc7962732f4
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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