Hydrochloric Acid → HCID 22400396, compound

HRID 2254286Notes

Reaction equation

HRID 2254286 reaction equation
Cl.C(=O)(O)[O-].[Na+].[H-].[Na+].[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl[CH2:21][CH2:22][C:23]1[N:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:26]([S:36][CH2:37][CH2:38][CH3:39])=[N:25][CH:24]=1>CCOCC.CN(C)C=O>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][N:27]1[C:23]([CH2:22][CH2:21][CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([O:17][CH2:18][CH3:19])=[O:16])=[CH:24][N:25]=[C:26]1[S:36][CH2:37][CH2:38][CH3:39]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 22400429HCID 22400429, compound

Product 1

HCID 22400396HCID 22400396, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

The above hydrochloride was converted to the free base in ether with 5% sodium bicarbonate solution. To a suspension of sodium hydride (57 mg, 2.38 mmol) in dimethylformamide (3 mL) held at 0° C. under argon was added a solution of diethyl malonate (0.4 g, 2.5 mmol) in dimethylformamide (3 mL). The mixture was stirred at ambient temperature for 0.5 hour or until a clear solution resulted. Then, 5-(2-chloroethyl)-1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazole (0.61 g, 1.85 mmol) in dimethylformamide (5 mL) was added, and the mixture was heated at 95° C.-100° C. for 24 hours. The reaction was partitioned between water and ethyl acetate, and the organic layer was washed with water, dried, concentrated and the residue chromatographed to provide 0.6 q (71%) of diethyl 2-[1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl]ethylmalonate as an oil.

Workup

  1. customheld at 0° C. under argon
  2. customresulted
  3. temperaturethe mixture was heated at 95° C.-100° C. for 24 hours
  4. customThe reaction was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customthe residue chromatographed

Sources & evidence

ORD record
ord-610bba0b4798491d9c0f0347cc8cf7bb
Source dataset
uspto-grants-1993_08
Patent number
US05234917

Reaction notes

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