N-3-Bromopropylphthalimide → 2-[3-(Methylsulfanyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 2262262Notes

Reaction equation

HRID 2262262 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[CH3:16][S-:17].[Na+]>CS(C)=O.O>[CH3:16][S:17][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]1=[O:15]

Participants

5

Reactant 2

HCID 21611N-3-BromopropylphthalimideHCID 4378561Sodium methanethiolate

Product 1

HCID 134589972-[3-(Methylsulfanyl)propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a mixture of N-(3-bromopropyl)phthalimide (500 mg) in DMSO (8 mL) was added sodium thiomethoxide (144 mg) and the reaction stirred at room temperature for 16 h. Then with water (2 mL) was added and the mixture stirred at room temperature for 10 min. The reaction was diluted with water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined organics were washed with aqueous brine solution (2×20 mL), dried (MgSO4) and reduced in vacuo to give 2-(3-methylsulfanyl-propyl)-isoindole-1,3-dione as a white solid.

Workup

  1. stirringthe mixture stirred at room temperature for 10 min
  2. extractionextracted into ethyl acetate (2×20 mL)
  3. washThe combined organics were washed with aqueous brine solution (2×20 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-4729a27f5bf1481bb4cf6a9c8ff2f493
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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