Chlorosuccinimide → HCID 18969628, compound

HRID 399029Notes

Reaction equation

HRID 399029 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][C:18]([C:28]([F:31])([F:30])[F:29])=[CH:19][C:20]=2[S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][CH:11]=1>O1CCCC1>[Cl:1][C:19]1[C:20]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[NH:17][C:18]=1[C:28]([F:29])([F:31])[F:30]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18969596HCID 18969596, compound

Product 1

HCID 18969628HCID 18969628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Chlorosuccinimide (0.734 g, 5.5 mmol) is added to a solution of 2-(p-chlorophenyl)-3-(phenylthio)-5-(trifluoromethyl)pyrrole (1.77 g, 5 mmol) in tetrahydrofuran. The reaction mixture is stirred overnight at room temperature, concentrated in vacuo, diluted with carbon tetrachloride and filtered. The resultant filtrate is 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 a yellow syrup which is identified by 1H NMR spectral analysis.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with carbon tetrachloride
  3. filtrationfiltered
  4. concentrationThe resultant filtrate is concentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-97d37a43bf1a41088f6fa27370ea79cd
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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