Phthalimide → 2-Phenylethyl-ethyl-disulphide

HRID 426585Notes

Reaction equation

HRID 426585 reaction equation
[CH2:1]([SH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N1C(=O)C2=CC=CC=[C:14]2[C:13]1=[S:22])C.C1(=O)NC(=O)C2=CC=CC=C12>C1C=CC=CC=1>[C:3]1([CH2:2][CH2:1][S:9][S:22][CH2:13][CH3:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 781262-PhenylethanethiolHCID 57251189N-ethylthiophthalimide

Product 1

HCID 203064362-Phenylethyl-ethyl-disulphideYield 111.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

8 g (0.058 mol) of phenethylmercaptan are added with intensive stirring to a suspension of 12 g (0.058 mol) of N-ethylthiophthalimide in 70 ml of benzene. After a few minutes, a homogeneous solution forms and the phthalimide slowly begins to precipitate out therefrom. After stirring for 48 hours at room temperature, the mixture is filtered through a paper filter, the filtrate is concentrated in a vacuum and the crude 2-phenylethyl-ethyl-disulphide (12.8 g) obtained is distilled through a Vigreux column. There are thus obtained 10.5 g of pure product (91% of theory) which has a purity of 99% (gas-chromatographic estimation). Boiling point 87-88 mm Hg/0.04 mm Hg; nD20 =1.5742.

Workup

  1. waitAfter a few minutes
  2. customto precipitate out
  3. filtrationthe mixture is filtered through a paper
  4. filtrationfilter
  5. concentrationthe filtrate is concentrated in a vacuum

Sources & evidence

ORD record
ord-05445a39f4be4c6e8130d9856d7d6cd7
Source dataset
uspto-grants-1979_10
Patent number
US04170594

Reaction notes

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