4-Chlorobenzenesulfenylchloride → HCID 18969586, compound

HRID 399030Notes

Reaction equation

HRID 399030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]Cl)=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([S:23][C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 110844654-ChlorobenzenesulfenylchlorideHCID 18969610HCID 18969610, compound

Product 1

HCID 18969586HCID 18969586, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(p-chlorophenyl)-3-nitropyrrole (4.88 g, 21.9 mmol) in methylene chloride is cooled to 0° C., treated dropwise over 30 minutes with a solution of p-chlorophenylsulfenyl chloride (4.32 g, 24 mmol) in methylene chloride, stirred at 0° C. for 3 hours, stirred overnight at room temperature, diluted with methylene chloride, washed sequentially with water, saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark residue. Flash column chromatography of the residue using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as a yellow solid (2.38 g, mp 195°-197° C.).

Workup

  1. stirringstirred overnight at room temperature
  2. washwashed sequentially with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a dark residue

Sources & evidence

ORD record
ord-38dbe27cd2894ec09d1645fa0b13765c
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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