4-Chlorobenzenesulfonyl chloride → alpha-(4-Chlorophenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850255Notes

Reaction equation

HRID 850255 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.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(#N)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([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:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Product 1

HCID 53754787alpha-(4-Chlorophenylsulfonyloxyimino)-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 12.2 g (0.055 mol) of 4-chlorobenzenesulfonic acid chloride in the presence of triethylamine. After recrystallisation of the crude product from ethyl acetate/hexane, 15.9 g (84%) of α-(4-chlorophenyl-sulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of yellowish crystals having a melting point of 145.5-148.5° 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 350 nm (ε=11660) that extends to 437 nm. Elemental analysis: C16H13ClN2O5S (380.80)

Workup

  1. customAfter recrystallisation of the crude product from ethyl acetate/hexane, 15.9 g (84%) of α-(4-chlorophenyl-sulfonyloxyimino)-3,4-dimethoxybenzyl cyanide
  2. customare obtained in the form of yellowish crystals

Sources & evidence

ORD record
ord-ffa653d4e3a4463ba748d63b2e430e82
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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