N-(4-Bromobutyl)phthalimide → N-(4-METHYLSULFANYL-BUTYL)PHTHALIMIDE

HRID 723170Notes

Reaction equation

HRID 723170 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[CH3:17][S-:18].[Na+]>CO>[CH3:17][S:18][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16]

Participants

4

Reactant 2

HCID 93575N-(4-Bromobutyl)phthalimideHCID 4378561Sodium methanethiolate

Product 1

HCID 10964136N-(4-METHYLSULFANYL-BUTYL)PHTHALIMIDEYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-bromo-butyl)-isoindole-1,3-dione (1.00 g, 3.54 mmol) in MeOH (60 mL) was treated with sodium thiomethoxide (0.298 g, 4.25 mmol) and heated to reflux 18 h. The solvent was evaporated in vacuo and the residue partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc (1×75 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to afford the product 2-(4-methylsulfanyl-butyl)-isoindole-1,3-dione (0.803 g, 91%). 1H NMR (MeOD) 7.844 (m, 4H), 3.704 (t, 2H, J=7.2 Hz), 2.549 (t, 2H, J=7.2 Hz), 2.063 (s, 3H), 1.792 (quint, 2H, J=7.2 Hz), 1.731 (quint, 2H, J=7.2 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux 18 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. extractionThe aqueous layer was further extracted with EtOAc (1×75 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fac5d27bd574830a23c8f29c19ef8f1
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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