Bromine → HCID 19754580, compound

HRID 1588801Notes

Reaction equation

HRID 1588801 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH2:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[CH:14]1.[Br:24]Br>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH2:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]1[Br:24]

Participants

4

Reactant 2

HCID 24408BromineHCID 19754602HCID 19754602, compound

Product 1

HCID 19754580HCID 19754580, compoundYield 13.62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.35 g (3.40 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-amino-4-trifluoromethylsulfenylimidazole in 20 ml of chloroform was added 0.5 ml (9.76 mmole) of bromine. The resulting mixture was stirred at RT under a nitrogen atmosphere for 2 hr. The mixture was then evaporated to remove the excess of bromine and the residue was partioned between water and methylene chloride. The organic layer was dried over anhydrous sodium sulfate and solvent was removed. The residue was purified by flash column chromatography on silica gel using 7% ethyl acetate in hexane to give 200 mg (13.62% yield) of the desired product, mp 154° C.

Workup

  1. customThe mixture was then evaporated
  2. customto remove the excess of bromine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvent
  4. customwas removed
  5. customThe residue was purified by flash column chromatography on silica gel using 7% ethyl acetate in hexane

Sources & evidence

ORD record
ord-410bf7b0dd674be388402a6887338c1e
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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