Water → HCID 178506191, compound

HRID 1591094Notes

Reaction equation

HRID 1591094 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([Cl:20])[C:11]=1[C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.O>CN(C)C=O>[Br:1][C:24]1[N:25]=[C:21]([C:11]2[C:12]([Cl:20])=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][C:10]=2[Cl:9])[NH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 18947716HCID 18947716, compound

Product 1

HCID 178506191HCID 178506191, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (0.63 g, 0.0036 mol) in dimethylformamide (dried over 4Å molecular sieve, 18 ml was added dropwise with stirring to a solution of 2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole (1.0 g, 0.0036 mol) in dimethylformamide (dried over 4Å molecular sieve, 18 ml) and stirred for 7 hours. The mixture was poured into water (180 ml) and extracted with dichloromethane (5×30 ml). The combined extracts were washed with water (3×50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by mplc on silica eluted with a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (3:5) to give 4-bromo-2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole (0.17 g), m.p. 224°-225° C., as an off-white solid.

Workup

  1. additionwas added dropwise
  2. extractionextracted with dichloromethane (5×30 ml)
  3. washThe combined extracts were washed with water (3×50 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customThe residue was purified by mplc on silica
  7. washeluted with a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (3:5)

Sources & evidence

ORD record
ord-9340dd787e0a40a2b10783f14f215595
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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