Thionyl Chloride → 3,5-dichloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-1,3-dihydro-2H-indol-2-one

HRID 1662598Notes

Reaction equation

HRID 1662598 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:26])([F:25])[F:24])(=[O:13])=[O:12])[C:6](=[O:27])[C:5]2(O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].S(Cl)([Cl:39])=O>C(Cl)(Cl)Cl>[Cl:39][C:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[N:7]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][C:23]([F:24])([F:26])[F:25])(=[O:13])=[O:12])[C:6]1=[O:27]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 674298505-chloro-3-hydroxy-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-1,3-dihydro-2H-indol-2-one

Product 1

HCID 674293293,5-dichloro-3-(2-methoxyphenyl)-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-1,3-dihydro-2H-indol-2-oneYield 84.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.00 g of compound obtained in Step 7-2-2 in CHCl3 (30 ml) was added sequentially 654 mg of Py and 984 mg of thionyl chloride under ice cooling, and the reaction mixture was stirred for 2 hours at the same temperature. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v) to obtain 2.63 g of the title compound (orange color solid).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v)

Sources & evidence

ORD record
ord-6f786cfeef314e5188e46f59c5ccbcf5
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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