Triethylamine → HCID 54161335, compound

HRID 850261Notes

Reaction equation

HRID 850261 reaction equation
[OH:1][N:2]=[C:3]([C:12]#[N:13])[C:4]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:21][CH:22]([S:24](Cl)(=[O:26])=[O:25])[CH3:23]>>[CH3:21][CH:22]([S:24]([O:1][N:2]=[C:3]([C:12]#[N:13])[C:4]1[CH:5]=[CH:6][C:7]([S:10][CH3:11])=[CH:8][CH:9]=1)(=[O:26])=[O:25])[CH3:23]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 59115184HCID 59115184, compound

Product 1

HCID 54161335HCID 54161335, compoundYield 83%

Procedure

Analogously to the preparation of Example 3.4, 9.6 g (0.5 mol) of α-hydroxyimino-4-methylthiobenzyl cyanide are reacted, in the presence of 7.6 g (0.075 mol) of triethylamine, with 7.85 g (0.055 mol) of 2-propanesulfonyl chloride. After working-up, the crude product is recrystallised from acetic acid acetate/hexane. 11.1 g (83%) of α-(2-propylsulfonyloxyimino)-4-methylthiobenzyl cyanide are obtained in the form of beige crystals having a melting point of 83-87° 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=14660) that extends to 435 nm. Elemental analysis: C12H14N2O3S2 (266.32)

Workup

  1. customthe crude product is recrystallised from acetic acid acetate/hexane

Sources & evidence

ORD record
ord-9d7b7e4b5902445aae179b7418e3a481
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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