Imidazole → 1H-Imidazol-2-amine, 4,5-dihydro-N-(2,6-dichlorophenyl)-1-(3-pyridinylcarbonyl)-

HRID 2166827Notes

Reaction equation

HRID 2166827 reaction equation
N1C=CN=C1.[C:6](Cl)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[NH:23][C:24]1[NH:25][CH2:26][CH2:27][N:28]=1>O1CCCC1>[C:6]([N:28]1[CH2:27][CH2:26][N:25]=[C:24]1[NH:23][C:17]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=1[Cl:15])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 2803ClonidineHCID 82604Nicotinoyl chloride

Product 1

HCID 30619571H-Imidazol-2-amine, 4,5-dihydro-N-(2,6-dichlorophenyl)-1-(3-pyridinylcarbonyl)-Yield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.40 g (50 millimoles) of imidazole are dissolved in 25 ml of absolute tetrahydrofuran, a solution of 3.54 g (25 millimoles) of nicotinoyl chloride in 25 ml of absolute tetrahydrofuran is added dropwise at room temperature, and the mixture is stirred for a further 2 hours. The imidazole hydrochloride which has precipitated is then filtered off, the filter residue is washed with a small amount of anhydrous tetrahydrofuran, the combined filtrates are added to a solution of 4.6 g (20 millimoles) of 2-(2',6'-dichlorophenylamino)-2-imidazoline in 25 ml of absolute tetrahydrofuran, and the mixture is stirred overnight. The solvent is then stripped off under reduced pressure on a rotary evaporator and the residue is twice recrystallized from isopropanol. 4.8 g of pure 1-nicotinoyl-2-(2',6'-dichlorophenylamino)-2-imidazoline of melting point 172.5°-174° C. are obtained; the material is identical with the product described in Example 1.

Workup

  1. customThe imidazole hydrochloride which has precipitated
  2. filtrationis then filtered off
  3. washthe filter residue is washed with a small amount of anhydrous tetrahydrofuran
  4. stirringthe mixture is stirred overnight
  5. customThe solvent is then stripped off under reduced pressure on a rotary evaporator
  6. customthe residue is twice recrystallized from isopropanol

Sources & evidence

ORD record
ord-4c6d172a25be4ccbbffd592ee14265f9
Source dataset
uspto-grants-1983_06
Patent number
US04389403

Reaction notes

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