Thionyl Chloride → 1-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid chloride

HRID 1646460Notes

Reaction equation

HRID 1646460 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:21](=[O:22])[CH:20]3[C:15](=[CH:16][CH2:17][CH2:18][CH2:19]3)[C:14]2=[O:23])=[CH:8][C:7]=1[S:24][C:25]1([C:28](O)=[O:29])[CH2:27][CH2:26]1>CN(C)C=O.C(Cl)CCl>[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:21](=[O:22])[CH:20]3[C:15](=[CH:16][CH2:17][CH2:18][CH2:19]3)[C:14]2=[O:23])=[CH:8][C:7]=1[S:24][C:25]1([C:28]([Cl:3])=[O:29])[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 678545381-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid

Product 1

HCID 1317177131-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

While stirring at room temperature, 3 ml of thionyl chloride are added to a solution of 1 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid and one drop of dimethylformamide in 40 ml of ethylene chloride and the reaction mixture is then heated under reflux for 3 hours. Concentration of the reaction mixture by evaporation yields 1 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid chloride in the form of an oil.

Workup

  1. temperaturethe reaction mixture is then heated
  2. temperatureunder reflux for 3 hours
  3. customConcentration of the reaction mixture by evaporation

Sources & evidence

ORD record
ord-2cc8c13a9b974eba80c968f28352c6ee
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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