Dimethylformamide → {2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl]methyl dimethyldithiocarbamate

HRID 129625Notes

Reaction equation

HRID 129625 reaction equation
[Br:1][C:2]1[N:3]([CH2:22]Cl)[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:5]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])[C:6]=1[Br:7].[OH-].[Na+].O.O.[CH3:28][N:29]([CH3:33])[C:30](=[S:32])[S-:31].[Na+].CN(C)C=O>O>[CH3:28][N:29]([CH3:33])[C:30](=[S:31])[S:32][CH2:22][N:3]1[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:5]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])[C:6]([Br:7])=[C:2]1[Br:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 152784222,3-Dibromo-1-(chloromethyl)-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrroleHCID 23693613Sodium dimethyldithiocarbamate dihydrate

Product 1

HCID 18930410{2,3-Dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrol-1-yl]methyl dimethyldithiocarbamateYield 31.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-Dibromo-1-(chloromethyl)-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole (1.0 g, 0.00194 mol) is added to a mixture of sodium hydroxide (0.084 g, 0.0021 mol), sodium dimethyldithiocarbamate dihydrate (0.376 g, 0.0021 mol) and dimethylformamide. The reaction mixture is stirred for six hours at room temperature, poured into water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a yellow gum. The gum is stirred with hexanes overnight and filtered to give the title product as a white solid (0.37 g, mp 185°-187° C.) which is identified by 1HNMR and 19FNMR spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow gum
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7ba1e84751b443c09403437f8dd6618b
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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