Acetone → HCID 86736123, compound

HRID 1112568Notes

Reaction equation

HRID 1112568 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Na].[C:7]([C:9](=[N:18][OH:19])[C:10]1[C:15]([Cl:16])=C[CH:13]=[CH:12][C:11]=1[Cl:17])#[N:8].[CH3:20]C(C)=O>>[CH3:20][O:19][N:18]=[C:9]([C:7]#[N:8])[C:10]1[CH:15]([Cl:16])[C:1](=[S:2](=[O:4])=[O:3])[CH:13]=[CH:12][C:11]=1[Cl:17]

Participants

5

Reactant 4

HCID 180AcetoneHCID 31297Methanesulfonyl chlorideHCID 5360545SodiumHCID 74383124HCID 74383124, compound

Product 1

HCID 86736123HCID 86736123, compound

Conditions

Temperature
25 °C

Procedure

A 3.3 g (0.028 mol) sample of methylsulfonyl chloride was added slowly to a slurry of 6.5 g (0.027 mol) of the sodium salt of alpha-cyano-2,6-dichlorobenzaldoxime in 60 ml acetone. The reaction was exothermic. After the addition was completed, the reaction mixture was stirred at about 25° C. for 1 hour, filtered and evaporated under reduced pressure to give a tan oil which crystallized to give the product. Recrystallization from ether/hexane gave the product as white crystals, m.p. 81-82. Nuclear magnetic resonance analysis showed the product to be approximately a 60:40 mixture of the syn- and anti-isomers. Elemental analysis for the product is tabulated in Table I as Compound No 3.

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customto give a tan oil which
  5. customcrystallized
  6. customto give the product
  7. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-bb9d7052afdf4002baaf53b2b336320c
Source dataset
uspto-grants-1978_10
Patent number
US04123255

Reaction notes

Loading…