2-Naphthalenethiol → N-[6-(2-naphthylthio)hexyl]phthalimide

HRID 54915

Reaction equation

HRID 54915 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[SH:17].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Cl.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.[K]>CN(C)C=O.O>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[S:17][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:30]1[C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]2[C:26]1=[O:36]

Participants

7

Reactant 4

HCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 805161-Bromo-6-chlorohexaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 19956979N-[6-(2-naphthylthio)hexyl]phthalimideYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (8.29 g) was added to a solution of 2-naphthalenethiol (8.01 g) and 1-bromo-6-chlorohexane (9.98 g) in N,N-dimethylformamide (65 ml). The mixture was stirred at room temperature for 3 hours. Then potassium phthalimide (9.26 g) was added to the mixture, and the resulting mixture was stirred at 100° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and the solvent was distilled off under reduced pressure to obtain N-[6-(2-naphthylthio)hexyl]phthalimide (18.56 g, 95.3%), which was then recrystallized from ethyl acetate-hexane. Colorless plate, mp: 109°-110° C.

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-04dc9cd25c024ef0ba055288c5c663ad
Source dataset
uspto-grants-1997_04
Patent number
US05624917

Linked notes

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