Imidazole → HCID 86736132, compound

HRID 1703441Notes

Reaction equation

HRID 1703441 reaction equation
Cl[CH:2]([NH:9][C:10](=[O:19])[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18])[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.C(N(CC)CC)C.[C:32]1([S:46]([OH:49])(=[O:48])=[O:47])[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([S:42]([OH:45])(=[O:44])=[O:43])[C:36]=2[CH:35]=[CH:34][CH:33]=1>O1CCCC1.CC(C)=O>[Cl:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:18])[C:11]=1[C:10]([NH:9][CH2:2][CH2:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:19].[N:20]1([CH2:2][C:3](=[O:8])[CH2:4][CH3:5])[CH:24]=[CH:23][N:22]=[CH:21]1.[C:32]1([S:46]([O-:49])(=[O:48])=[O:47])[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([S:42]([O-:45])(=[O:44])=[O:43])[C:36]=2[CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 66661,5-Naphthalenedisulfonic acidHCID 8471TriethylamineHCID 22761233HCID 22761233, compound

Product 1

HCID 86736132HCID 86736132, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

152 g (0.5 mol) of 1-chloro-1-(2,6-dichlorobenzamido)-3,3-dimethyl-butan-2-one in 300 ml of tetrahydrofuran were added dropwise in the course of one hour at 10° C., to a suspension of 70 g (1.1 mol) of imidazole and 70 ml (0.5 mol) of triethylamine in 300 ml of tetrahydrofuran. The mixture was stirred for 15 hours at room temperature and filtered, and the residue was rinsed with ethyl acetate. The filtrate was concentrated in a waterpump vacuum and the residue was taken up in 500 ml of methylene chloride and washed three times with 200 ml water at a time. After drying over sodium sulphate, the solvent was distilled off in a waterpump vacuum. The oil which remained was dissolved in 500 ml of acetone and 90 g (0.3 mol) of 1,5-naphthalenedisulphonic acid in acetone were added. The crystals which precipitated were filtered off and washed with acetone/water (10:1). 14.9 g (21.8% of theory) of 1-(2,6-dichlorobenzamido)-3,3-dimethylbutan-1-(imidazol-1-yl)-butan-2-one-naphthalene-1,5-disulphonate of melting point 220°-230° C. (decomposition) were obtained.

Workup

  1. filtrationfiltered
  2. washthe residue was rinsed with ethyl acetate
  3. concentrationThe filtrate was concentrated in a waterpump vacuum
  4. washwashed three times with 200 ml water at a time
  5. dry with materialAfter drying over sodium sulphate
  6. distillationthe solvent was distilled off in a waterpump vacuum
  7. dissolutionThe oil which remained was dissolved in 500 ml of acetone
  8. customThe crystals which precipitated
  9. filtrationwere filtered off
  10. washwashed with acetone/water (10:1)

Sources & evidence

ORD record
ord-f8c5e0a69fbd4f1bb129c0abd36ece0c
Source dataset
uspto-grants-1978_11
Patent number
US04124369

Reaction notes

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