2-Mercaptoimidazole → 4-Bromo-2-(p-chlorophenyl)-1-[(imidazol-2-ylthio)methyl]-5-trifluoromethylpyrrole-3-carbonitrile hydrobromide

HRID 1198102Notes

Reaction equation

HRID 1198102 reaction equation
[Br:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:5]([CH2:11]Br)[C:6]=1[C:7]([F:10])([F:9])[F:8].[NH:22]1[CH:26]=[CH:25][NH:24][C:23]1=[S:27]>C(O)(C)C>[BrH:1].[Br:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:5]([CH2:11][S:27][C:23]2[NH:22][CH:26]=[CH:25][N:24]=2)[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

4

Reactant 2

HCID 12013862-MercaptoimidazoleHCID 110047254-Bromo-1-(bromomethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Product 1

HCID 189493914-Bromo-2-(p-chlorophenyl)-1-[(imidazol-2-ylthio)methyl]-5-trifluoromethylpyrrole-3-carbonitrile hydrobromideYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-bromo-1-(bromomethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (0.88g, 0.002 mol) and 4-imidazoline-2-thione (0.23g, 0.002 mol) in isopropanol is heated at reflux temperature for 3 hours, cooled to room temperature and filtered. The filtercake is washed with isopropanol and air-dried to give the title product as a white solid, 0.81 g (75% yield), mp 221°-223° C.(dec).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. filtrationfiltered
  4. washThe filtercake is washed with isopropanol
  5. customair-dried

Sources & evidence

ORD record
ord-c0dfdd3ab89f489684eab38700f2bf0f
Source dataset
uspto-grants-1994_01
Patent number
US05280021

Reaction notes

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