Water → alpha-(4-Dodecylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850251Notes

Reaction equation

HRID 850251 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.[CH2:16]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.O>O1CCCC1>[CH2:16]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([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:36])=[O:35])=[CH:32][CH:33]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 54260730alpha-(4-Dodecylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanideYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to the preparation of Example 1, 14.4 g (0.07 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted at room temperature with 26.56 g (0.077 mol) of 4-dodecylbenzenesulfonyl chloride in 100 ml of tetrahydrofuran in the presence of 10.6 g (0.105 mol) of triethylamine. For working-up, the reaction mixture is poured into water and extracted several times with methylene chloride. After drying over magnesium sulfate, the solvent is distilled off in a rotary evaporator. The brown oil that remains is then purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:1). 14.75 g (41%) of α-(4-dodecylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of a viscous yellow oil. The 1H-NMR spectrum shows that it is the (syn) isomer. The UV/Vis spectrum (acetonitrile) shows an absorption band at 350 nm (ε=10700) that extends to 435 nm. Elemental analysis: C28H38N2O5S

Workup

  1. extractionextracted several times with methylene chloride
  2. dry with materialAfter drying over magnesium sulfate
  3. distillationthe solvent is distilled off in a rotary evaporator
  4. customThe brown oil that remains is then purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-198a6c46f2744ba1a833f86e159da121
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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