Hydrochloric Acid → HCID 69418751, compound

HRID 1296361Notes

Reaction equation

HRID 1296361 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:10]=1)=[O:5].[CH3:27][Mg]I.Cl>C1COCC1.CCOCC>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([N:9]2[CH:10]=[C:6]([C:4](=[O:5])[CH3:27])[N:7]=[C:8]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86592992HCID 86592992, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 69418751HCID 69418751, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid methoxy-methyl-amide I-7e (1.64 g, 3.99 mmol) in THF (16 ml) was cooled to 0° C., and methylmagnesium iodide (4.4 ml of a 3.0 M solution in Et2O, 9.9 mmol) was added dropwise via syringe. The resultant solution was stirred at 0° C. for 1 h, and then the reaction mixture was poured into cold 1N HCl (100 ml). The mixture was extracted with ethyl acetate (2 85-ml portions), and the combined extracts were washed with saturated aqueous sodium chloride (100 ml). The organics were dried over anhydrous magnesium sulfate and were concentrated to afford 1-[1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanone I-7f (1.41 g, 97%) that was used in the next reaction without any further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2 85-ml portions)
  2. washthe combined extracts were washed with saturated aqueous sodium chloride (100 ml)
  3. dry with materialThe organics were dried over anhydrous magnesium sulfate
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-64f99208dd604dc28f41bdbcc5a96e17
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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