Pyridine → 4-(1,3-Dioxoisoindolin-2-yl)phenethyl 4-methylbenzenesulfonate

HRID 1023834Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:6][CH:5]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])=[CH:8][CH:9]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-(2-hydroxyethyl)phenyl)isoindoline-1,3-dione (926 mg, 3.46 mmol) was dissolved in dichloromethane (15 mL), cooled to 0° C. and p-toluenesulfonyl chloride (991 mg, 5.2 mmol) was added, followed by pyridine (0.56 ml, 6.93 mmol). The reaction was stirred at room temperature for 16 h and concentrated. The residue was dissolved in ethyl acetate (60 ml), washed with water (20 ml), saturated aqueous NaHCO3 (2×15 ml), brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude tosylate was used without further purification.

Workup

concentrationconcentrated
dissolutionThe residue was dissolved in ethyl acetate (60 ml)
washwashed with water (20 ml), saturated aqueous NaHCO3 (2×15 ml), brine (20 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude tosylate was used without further purification

Sources & evidence

ORD record: ord-420a9fcd0384438eb0e140f44e2bc9de
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722720B2

Reaction notes

Loading…