Pyridine → 7-(1,3-Dioxoisoindol-2-yl)heptyl-4-methylbenzenesulfonate

HRID 1911498Notes

Reaction equation

HRID 1911498 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19].C(Cl)Cl.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.N1C=CC=CC=1>O>[O:18]=[C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:19])[N:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 189709042-(7-Hydroxyheptyl)isoindoline-1,3-dione

Product 1

HCID 867621807-(1,3-Dioxoisoindol-2-yl)heptyl-4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

783 mg of 2-(7-hydroxyheptyl)isoindol-1,3-dione was added to 40 mL of DCM, and 800 mg of p-toluenesulfonyl chloride was added. Pyridine was then added dropwise with stirring, and the mixture was stirred overnight. After 24 h, 100 mL of water was added to the reaction system, which was then violently vibrated and isolated. The water layer was extracted with 50 mL of DCM. The organic layers were combined, successively washed with 100 mL of 5% citric acid aqueous solution, 100 mL of saturated sodium carbonate aqueous solution, and 100 mL of saturated sodium chloride aqueous solution, dried over 5 g of MgSO4 for 30 min, and concentrated via a rotary evaporator to obtain an oily liquid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. customviolently vibrated and isolated
  4. extractionThe water layer was extracted with 50 mL of DCM
  5. washsuccessively washed with 100 mL of 5% citric acid aqueous solution, 100 mL of saturated sodium carbonate aqueous solution, and 100 mL of saturated sodium chloride aqueous solution
  6. dry with materialdried over 5 g of MgSO4 for 30 min
  7. concentrationconcentrated via a rotary evaporator
  8. customto obtain an oily liquid

Sources & evidence

ORD record
ord-b637c823c2ff413faab16203db951f4c
Source dataset
uspto-grants-2013_12
Patent number
US08604065B2

Reaction notes

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