Water → HCID 11826288, compound

HRID 1700361Notes

Reaction equation

HRID 1700361 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[Br:7][C:8]1[NH:9][C:10]([Br:14])=[C:11]([CH3:13])[N:12]=1.[CH3:15][C:16]1[CH:21]=CC([N+]([O-])=O)=[CH:18][C:17]=1[S:25](Cl)(=[O:27])=[O:26].[OH2:29].[C:30](#[N:32])[CH3:31]>>[CH3:21][C:16]1[CH:15]=[C:30]([N+:32]([O-:2])=[O:29])[CH:31]=[CH:18][C:17]=1[S:25]([N:12]1[C:11]([CH3:13])=[C:10]([Br:14])[N:9]=[C:8]1[Br:7])(=[O:27])=[O:26]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 11430Potassium CarbonateHCID 178432451HCID 178432451, compound

Product 1

HCID 11826288HCID 11826288, compoundYield 51%

Procedure

1.4 g (10 mmol) of potassium carbonate are added to a solution of 1.7 g (7 mmol) of 2,5-dibromo-4-methyl-1H-imidazole in 40 ml of acetonitrile at room temperature. The mixture is stirred for 10 minutes at room temperature, and 1.7 g (7 mmol) of 2-methyl-5-nitro-benzenesulphonyl chloride are then added. Stirring is carried out for a further 20 hours at room temperature and the reaction mixture is then poured onto 100 ml of water. The mixture formed is extracted twice with 50 ml of diethylether in each case. The combined organic phases are dried over sodium sulphate and then evaporated down under reduced pressure. The remaining residue is chromatographed on silica gel using methylene chloride as mobile phase. 1.6 g (51% of theory) of 1-(2-methyl-4-nitro-benzenesulphonyl)-2,4-dibromo-5-methyl-1H-imidazole are obtained in this manner in the form of a colourless solid substance of melting point 187 to 189° C.

Workup

  1. stirringStirring
  2. waitis carried out for a further 20 hours at room temperature
  3. customThe mixture formed
  4. extractionis extracted twice with 50 ml of diethylether in each case
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customevaporated down under reduced pressure
  7. customThe remaining residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-331d4b26953e4aba866e30ea2bf07445
Source dataset
uspto-grants-2002_02
Patent number
US06350770B1

Reaction notes

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