Thiophenol → HCID 13252413, compound

HRID 647407Notes

Reaction equation

HRID 647407 reaction equation
Cl[CH:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[F:19].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:3]2[CH:2]([S:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[C:4]2=[O:11])=[C:13]([F:19])[CH:14]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 132576323-Chloro-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

Product 1

HCID 13252413HCID 13252413, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dichloromethane were dissolved 3.0 g of 3-chloro-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one and 1.1 g of thiophenol, and 1.0 g of triethylamine was added to the solution over a 10-minute period, followed by stirring at room temperature for 2 hours. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and freed of the dichloromethane under reduced pressure. The residue was purified by means of column chromatography with the use of silica gel (developing solvent of dichloromethaneacetone), thereby producing 3.2 g (yield of 86%) of the subject compound in white crystals, m.p. 86°-87° C.

Workup

  1. additionwas added to the solution over a 10-minute period
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue was purified by means of column chromatography with the use of silica gel (developing solvent of dichloromethaneacetone)

Sources & evidence

ORD record
ord-a77da4258fe1423584ede4039290dd44
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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