Imidazole → HCID 86738385, compound

HRID 1065785Notes

Reaction equation

HRID 1065785 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[C:6](=[O:17])[CH:7](Br)[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[C:26]1([S:40]([OH:43])(=[O:42])=[O:41])[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([S:36]([OH:39])(=[O:38])=[O:37])[C:30]=2[CH:29]=[CH:28][CH:27]=1>C(#N)C.CC(C)=O>[C:26]1([S:40]([OH:43])(=[O:42])=[O:41])[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([S:36]([OH:39])(=[O:38])=[O:37])[C:30]=2[CH:29]=[CH:28][CH:27]=1.[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[C:6](=[O:17])[CH:7]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 66661,5-Naphthalenedisulfonic acidHCID 53994102HCID 53994102, compound

Product 1

HCID 86738385HCID 86738385, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

145 g (0.4 mol) of 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-keto-butanoic acid ethyl ester were dissolved in 800 ml of acetonitrile. 100 g (1.45 mol) of imidazole were added and the mixture was heated for 20 hours under reflux. The solvent was then distilled off in vacuo, the residue was taken up in 500 ml of methylene chloride and the solution was washed three times with 200 ml of water each time, dried over sodium sulphate and concentrated. The oil which remained was dissolved in 800 ml of acetone and 100 g (0.35 mol) of 1,5-naphthalenedisulphonic acid in 300 ml of acetone were added. The resulting crystalline precipitate was filtered off and dried. 122.5 g (62% of theory) of 4-(4-chlorophenoxy)-2,2-dimethyl-4-(imidazol-1-yl)-3-keto-butanoic acid ethyl ester 1,5-naphthalenedisulphonate of melting point 194° C. were obtained.

Workup

  1. temperaturethe mixture was heated for 20 hours
  2. temperatureunder reflux
  3. distillationThe solvent was then distilled off in vacuo
  4. washthe solution was washed three times with 200 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. dissolutionThe oil which remained was dissolved in 800 ml of acetone
  8. filtrationThe resulting crystalline precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-6e13aa2393064174b5305e6190fc0338
Source dataset
uspto-grants-1982_05
Patent number
US04331674

Reaction notes

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