4-Methylbenzenethiol → HCID 420617, compound

HRID 1741441Notes

Reaction equation

HRID 1741441 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][N:14]1C(=O)C2=CC=CC=C2C1=O>O1CCCC1.ClCCl>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][CH2:13][NH2:14])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 24758Sodium hydride

Product 1

HCID 420617HCID 420617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

1.04 g (43.4 mmol) of NaH was dissolved in 40 ml of tetrahydrofuran at 0° C. To the resulting solution, 4 ml of 4-methylthiophenol dissolved in dry tetrahydrofuran was added slowly. The resultant mixture was stirred at an ambient temperature for 20 minutes and 8.0 g (31 mnol) of N-(2-bromoethyl)phthalimide obtained in step 1 dissolved in dry tetrahydrofuran was added. The mixture was stirred overnight at an ambient temperature and then refluxed for 2 hours. The reaction mixture was distilled under a reduced pressure to produce a residue, which was dissolved in dichloromethane. Then, the resultant solution was washed with water and with an aqueous sodium chloride solution. The organic layer was dried and dichloromethane was removed under a reduced pressure. The residue was recrystallized from a mixture of ethyl acetate/hexane to obtain 6.86 g of the title compound as a yellow solid. The solution remaining after the recrystallization was purified by column chromatography (eluent; ethyl acetate: hexane=1:6) to obtain additional 1.40 g of the title compound. Therefore, a total of 8.26 g (yield 90%) of the title compound was obtained.

Workup

  1. additionwas added slowly
  2. additionwas added
  3. temperaturerefluxed for 2 hours
  4. distillationThe reaction mixture was distilled under a reduced pressure
  5. customto produce a residue, which
  6. washThen, the resultant solution was washed with water and with an aqueous sodium chloride solution
  7. customThe organic layer was dried
  8. customdichloromethane was removed under a reduced pressure
  9. customThe residue was recrystallized from a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-21c84643ecf040128b2cfb6fda72a52c
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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