HCID 20087063, compound → HCID 20087055, compound

HRID 1608694Notes

Reaction equation

HRID 1608694 reaction equation
[C:1]([CH2:3][CH:4]([CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:5]OS(C1C=CC(C)=CC=1)(=O)=O)#[N:2].[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>CS(C)=O>[C:1]([CH2:3][CH:4]([CH2:5][S:31][C:29](=[O:32])[CH3:30])[CH2:17][S:31][C:29](=[O:32])[CH3:30])#[N:2]

Participants

4

Reactant 2

HCID 20087063HCID 20087063, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20087055HCID 20087055, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of 62 g of 2-cyanomethyl-1,3-bis(tosyloxy)propane in 250 ml DMSO is added dropwise to a stirred solution of 36 g potassium thioacetate in 200 ml of DMSO. After stirring for one hour and adding additional DMSO, the mixture is poured into ice/water. Extraction with diethylether yields a colored organic layer which is washed successively with aqueous NaOH, water and saturated NaCl solution until neutral. Drying and evaporating yields the desired 2-cyanomethyl-1,3-bis(acetylthio)propane as a slightly yellow liquid; b.p. 146°-150° C./0.50.1 mm Hg; yield 20 g. Identification by IR and NMR.

Workup

  1. extractionExtraction with diethylether
  2. customyields a colored organic layer which
  3. washis washed successively with aqueous NaOH, water and saturated NaCl solution until neutral
  4. customDrying
  5. customevaporating

Sources & evidence

ORD record
ord-b10e0bf263444af09ff013ec0e7805ba
Source dataset
uspto-grants-1995_03
Patent number
US05395946

Reaction notes

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