2-Propanesulfonyl chloride → alpha-(2-Propylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850252Notes

Reaction equation

HRID 850252 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][CH:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18]>C(N(CC)CC)C>[CH3:16][CH:17]([S:19]([O: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)(=[O:21])=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 53791302alpha-(2-Propylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanideYield 88%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described under 1.2, 16.5 g (0.08 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 12.6 g (0.088 mol) of 2-propanesulfonyl chloride in the presence of triethylamine. Recrystallisation of the crude product from ethyl acetate/hexane yields 21.9 g (88%) of α-(2-propylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide in the form of beige crystals having a melting point of 90.5-93.5° 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 346 nm (ε=1165034) that extends to 434 nm. Elemental analysis: C13H16N2O5S (312.34)

Workup

  1. customRecrystallisation of the crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-857837a0f34b4f4db2dad1eb29c77d26
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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