Thionyl Chloride → HCID 51351392, compound

HRID 2381575Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 51349563HCID 51349563, compound

Product 1

HCID 51351392HCID 51351392, compoundYield 100%

Procedure

2-(4-Chlorobenzyl)-3-(4-chlorophenyl)-3-hydroxyisoindolinone (150 mg, 0.390 mmol.) was reacted with thionyl chloride (0.031 mL, 0.429 mmol.) and a catalytic amount of DMF as for general procedure B, and the solvent removed to give a colourless oil of the crude 3-chloro-2-(4-chlorobenzyl)-3-(4-chlorophenyl)isoindolin-1-one (157 mg, 0.390 mmol., 100%).

Workup

customa catalytic amount of DMF as for general procedure B, and the solvent removed

Sources & evidence

ORD record: ord-b6535ae734ec46f694654e7edb72d3eb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258175B2

Reaction notes

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