1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 12751899, compound

HRID 2262258Notes

Reaction equation

HRID 2262258 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[CH3:15][S-:16].[Na+]>CS(C)=O.O>[CH3:15][S:16][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:14]

Participants

5

Reactant 2

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 4378561Sodium methanethiolate

Product 1

HCID 12751899HCID 12751899, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a mixture of N-(2-bromoethyl)phthalimide (500 mg) in DMSO (8 mL) was added sodium thiomethoxide (152 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-(2-methylsulfanyl-ethyl)-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-c2e8cb0e0de146c6bee3b67f2a081b1e
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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