Thionyl Chloride → HCID 51349421, compound

HRID 2381572Notes

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 51349836HCID 51349836, compound

Product 1

HCID 51349421HCID 51349421, compoundYield 100%

Procedure

3-(4-Chlorophenyl)-3-hydroxy-2-phenethylisoindolin-1-one (250 mg, 0.687 mmol.) was reacted with thionyl chloride (0.055 mL, 0.756 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-3-(4-chlorophenyl)-2-phenethylisoindolin-1-one (256 mg, 0.687 mmol., 100%).

Workup

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

Sources & evidence

ORD record: ord-5ceba8e9a8f74e42bf40d7e5e5aad638
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258175B2

Reaction notes

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