Imidazole → HCID 13176303, compound

HRID 1981305Notes

Reaction equation

HRID 1981305 reaction equation
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1>C(#N)C.CC(C)=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH:2]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 66661,5-Naphthalenedisulfonic acidHCID 13176302HCID 13176302, compound

Product 1

HCID 13176303HCID 13176303, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent2×

Procedure

23 g of crude 5-bromo-5-(4-chlorophenoxy)-3,3-dimethylpent-1-en-4-one, dissolved in 30 ml of acetonitrile, were added dropwise to a solution of 28.6 g (0.42 mol) of imidazole in 250 ml of acetonitrile, in the course of 5 minutes. The mixture was then heated to the boil for a further 3 hours and the solution was concentrated under reduced pressure. The oily residue was taken up in 200 ml of ethyl acetate and the mixture was washed with three times 50 ml of water. After the organic phase had been dried over anhydrous sodium sulphate, it was concentrated by evaporation, the residue was taken up in 200 ml of acetone and a filtered solution of 20.2 g (0.07 mol) of naphthalene-1,5-disulphonic acid in 100 ml of acetone was added. The precipitated salt was filtered off under suction, 100 ml of water and 100 ml of dichloromethane were added to it, and the mixture was then rendered alkaline with 10% strength sodium carbonate solution. The organic phase was separated off and concentrated. The oily residue crystallized on trituration with ether/petroleum ether. 7.4 g (34.7% of theory) of 5-(4-chlorophenoxy)-3,3-dimethyl-5-(imidazol-1-yl)-pent-1-en-4-one of melting point 72° to 74° C. were obtained.

Workup

  1. temperatureThe mixture was then heated to the boil for a further 3 hours
  2. concentrationthe solution was concentrated under reduced pressure
  3. washthe mixture was washed with three times 50 ml of water
  4. dry with materialAfter the organic phase had been dried over anhydrous sodium sulphate, it
  5. concentrationwas concentrated by evaporation
  6. filtrationThe precipitated salt was filtered off under suction, 100 ml of water and 100 ml of dichloromethane
  7. additionwere added to it
  8. customThe organic phase was separated off
  9. concentrationconcentrated
  10. customThe oily residue crystallized on trituration with ether/petroleum ether

Sources & evidence

ORD record
ord-3ddd9cb462a7420c82f145b2aab9a575
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

Loading…