Triethylamine → alpha-(2,4,6-Tris(isopropyl)phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850253Notes

Reaction equation

HRID 850253 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.[CH:16]([C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[C:21]([CH:28]([CH3:30])[CH3:29])[C:20]=1[S:31](Cl)(=[O:33])=[O:32])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[CH:16]([C:19]1[CH:24]=[C:23]([CH:25]([CH3:26])[CH3:27])[CH:22]=[C:21]([CH:28]([CH3:30])[CH3:29])[C:20]=1[S:31]([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:33])=[O:32])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 53824454alpha-(2,4,6-Tris(isopropyl)phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As described under 1.2, 8.25 g (0.04 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 13.3 g (0.044 mol) of 2,4,6-tris(isopropyl)benzenesulfonyl chloride in the presence of triethylamine. After recrystallisation of the crude product from ethyl acetate/-hexane, 14.25 g (75%) of α-(2,4,6-tris(isopropyl)phenylsulfonyl-oxyimino)-3,4-dimethoxy-benzyl cyanide are obtained 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 352 nm (ε=11000) that extends to 433 nm. Elemental analysis: C25H32N2O5S (472.6)

Workup

  1. customAfter recrystallisation of the crude product from ethyl acetate/-hexane, 14.25 g (75%) of α-(2,4,6-tris(isopropyl)phenylsulfonyl-oxyimino)-3,4-dimethoxy-benzyl cyanide
  2. customare obtained in the form of beige crystals

Sources & evidence

ORD record
ord-c9104e84d49949b28b13b9a73e116423
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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