Triethylamine → 2-(p-Chlorophenyl)-4-[(3,4-dichlorophenyl)thio]-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 399034Notes

Reaction equation

HRID 399034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]Cl)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:19][C:20]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:22]=2[C:23]#[N:24])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[NH:19][C:20]([C:25]([F:28])([F:26])[F:27])=[C:21]([S:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:22]=2[C:23]#[N:24])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrileHCID 128785403,4-Dichlorobenzenesulfenyl chloride

Product 1

HCID 189695992-(p-Chlorophenyl)-4-[(3,4-dichlorophenyl)thio]-5-(trifluoromethyl)pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dichlorophenylsulfenyl chloride (1.6 g, 7.49 mmol) is added to a solution of 2-(p-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile (2.02 g, 7.48 mmol) and triethylamine (1.67 g, 16.5 mmol) in methylene chloride. The reaction mixture is stirred at room temperature for 24 hours and concentrated in vacuo to obtain a residue. The residue is slurried in ethyl acetate and the resultant mixture is filtered to remove solids. The filtrate is diluted with hexanes to precipitate a solid which is collected and dried to give the title product as a cream colored solid (mp 94°-97° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a residue
  3. filtrationthe resultant mixture is filtered
  4. customto remove solids
  5. additionThe filtrate is diluted with hexanes
  6. customto precipitate a solid which
  7. customis collected
  8. customdried

Sources & evidence

ORD record
ord-81d168ca8998475b8275eb45dc79eac9
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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