HCID 10999322, compound → HCID 10960055, compound

HRID 399025Notes

Reaction equation

HRID 399025 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[CH:13][CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][C:21]=2[S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 10999322HCID 10999322, compoundHCID 110844654-Chlorobenzenesulfenylchloride

Product 1

HCID 10960055HCID 10960055, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of p-chlorophenylsulfenyl chloride (0.80 g, 4.48 mmol) in methylene chloride is added dropwise over 20 minutes to a stirred solution of 2-(p-chlorophenyl)-5-trifluoromethylpyrrole (1.0 g, 4.07 mmol) in methylene chloride. The reaction mixture is stirred at room temperature for 90 minutes, diluted with methylene chloride, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 1:10 ethyl acetate/hexanes solution gives the title product as an off-white solid (0.96 g, mp 39°-54° C.).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-44f91d2b5397479f909c561e8d357f6f
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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