Thionyl Chloride → HCID 59824783, compound

HRID 2381569Notes

Reaction equation

HRID 2381569 reaction equation
[CH2:1]([N:8]1[C:16](O)([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:19][CH:18]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:36])=O>CN(C=O)C>[CH2:1]([N:8]1[C:16]([Cl:36])([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:19][CH:18]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 16090426HCID 16090426, compound

Product 1

HCID 59824783HCID 59824783, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

2-Benzyl-3-hydroxy-3-[4-(2-trimethylsilanylethoxymethoxy)phenyl]-2,3-dihydroiso-indol-1-one (125 mg, 0.27 mmol) was reacted with thionyl chloride (0.019 mL, 0.27 mmol) and a catalytic amount of DMF (3 drops) as for general procedure G. Removal of the solvent gave 2-benzyl-3-chloro-3-[4-(2 trimethylsilanylethoxymethoxy)phenyl]-2,3-dihydroiso-indol-1-one as a colourless oil (129 mg, 0.27 mmol, 100%).

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-bf1f74553063494891c5589343c52de7
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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