Imidazole → 1,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one

HRID 1995921Notes

Reaction equation

HRID 1995921 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7](Br)[C:8](=[O:21])[C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.O.O.O.O.C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1>C(#N)C.CC(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[C:8](=[O:21])[C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 127659701,4-Bis-(4-chlorophenoxy)-1-bromo-3,3-dimethyl-butan-2-oneHCID 53249422Naphthalene-1,5-disulfonic acid tetrahydrate

Product 1

HCID 127659761,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-oneYield 67.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

21.6 g (0.05 mol) of crude 1,4-bis-(4-chlorophenoxy)-1-bromo-3,3-dimethyl-butan-2-one were stirred under reflux with 14 g (0.2 mol) of imidazole in 100 ml of acetonitrile for 17 hours. The mixture was then concentrated by distilling off the solvent under reduced pressure. The residue was taken up in 400 ml of methylene chloride and the mixture was extracted by shaking three times with 800 ml of water each time, dried over sodium sulphate and concentrated. The residue was taken up in 100 ml of acetone and 9 g (0.05 mol) of 1,5-naphthalenedisulphonic acid tetrahydrate in 50 ml of acetone were added dropwise. The precipitate formed was filtered off and suspended in 200 ml of methylene chloride. 400 ml of saturated sodium bicarbonate solution were added, the mixture was stirred for 30 minutes and the organic phase was separated off. After distilling off the solvent, 14.1 g (67% of theory) of 1,4-bis-(4-chlorophenoxy)- 3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one were obtained as an oil.

Workup

  1. concentrationThe mixture was then concentrated
  2. distillationby distilling off the solvent under reduced pressure
  3. extractionthe mixture was extracted
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe precipitate formed
  7. filtrationwas filtered off
  8. addition400 ml of saturated sodium bicarbonate solution were added
  9. stirringthe mixture was stirred for 30 minutes
  10. customthe organic phase was separated off
  11. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-a3f13ca913424936aca2e5f719a24ed5
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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