2-(Cyclohexylthio)-1H-isoindole-1,3(2H)-dione → Phthalimide

HRID 435729

Reaction equation

HRID 435729 reaction equation
C1(S[N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])CCCCC1>CCCCCCC>[C:12]1(=[O:13])[NH:8][C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]12

Participants

3

Reactant 1

HCID 287772-(Cyclohexylthio)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

13.1 Grams (0.05 mole) of N-(cyclohexylthio)phthalimide and 6.9 grams (0.05 mole) of benzoyl thiol(thiobenzoic acid) in 150 ml of heptane are stirred overnight at room temperature. The precipitate is recovered by filtration, washed with carbon tetrachloride and dried. 7.3 Grams of phthalimide (m.p. 234° C) are obtained. The solvent is removed from the filtrate by evaporation under reduced pressure. 12 Grams (95% yield) of product, a light brown liquid, are obtained. The identity of the benzoylcyclohexyl disulfide is confirmed by GLC and NMR analyses. Analysis gives 25.51% sulfur compared to 25.45% sulfur calculated for C13H16OS2. Similarly, except N-(2-benzothiazolylthio)phthalimide is one reactant, there is obtained benzoyl-2-benzothiazolyl disulfide.

Workup

  1. filtrationThe precipitate is recovered by filtration
  2. washwashed with carbon tetrachloride
  3. customdried

Sources & evidence

ORD record
ord-1f3f968f02cf4a27bffac25feb1237a1
Source dataset
uspto-grants-1977_02
Patent number
US04006155

Linked notes

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