4-(4-Chlorophenoxy)aniline → 1-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione

HRID 1972186Notes

Reaction equation

[C:1]1(=[O:7])[O:6][C:4](=O)[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:9]=1.O=S(Cl)Cl>C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:10]2[CH:11]=[CH:12][C:13]([N:14]3[C:1](=[O:7])[CH2:2][CH2:3][C:4]3=[O:6])=[CH:8][CH:9]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of succinic anhydride (250 mg, 2.50 mmol) and 4-amino-4′-chloro diphenylether (500 mg, 2.27 mml) in toluene is heated to 110° C. for 14 h. and cooled down to room temperature. SOCl2 (1.5 mL) is added into the mixture and stirred at room temperature for 8 h. After the solvent is removed under vacuum, the residue is treated with saturated NaHCO3 aqueous solution (20 mL) and extracted with CHCl3 (3×50 mL). The combined organic layer is washed with brine and dried (MgSO4). After filtering the drying agent, the filtrate is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%) to provide 1-[4-(4-chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione as white solid (570 mg, 83%).

Workup

temperaturecooled down to room temperature
customAfter the solvent is removed under vacuum
additionthe residue is treated with saturated NaHCO3 aqueous solution (20 mL)
extractionextracted with CHCl3 (3×50 mL)
washThe combined organic layer is washed with brine
dry with materialdried (MgSO4)
filtrationAfter filtering the drying agent
concentrationthe filtrate is concentrated
custompurified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%)

Sources & evidence

ORD record: ord-27372413f40c435287ff7bf4b98e13d5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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