Hydrochloric Acid → HCID 66992896, compound

HRID 1254054Notes

Reaction equation

HRID 1254054 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2C=CC(C#N)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[CH3:29][Mg+].[Br-].Cl.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:11][C:10]=2[C:21]2[CH:35]=[CH:34][C:33]([C:37](=[O:36])[CH3:29])=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 44553222HCID 44553222, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 66992896HCID 66992896, compound

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 2, 35 mg, 0.087 mmol) in 0.75 mL of THF was added MeMgBr (3M in ether, 0.44 mmol) at 0° C. After heating at reflux for 2 hr, the reaction was cooled to rt and 5 mL 2N HCl was added, and was stirred for another hour. The reaction was quenched with aqueous sodium bicarbonate (pH=ca 7). The product was extracted with EtOAc, the combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to dryness to give 1-(4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}phenyl)ethanone, which was used in the next step without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hr
  3. customThe reaction was quenched with aqueous sodium bicarbonate (pH=ca 7)
  4. extractionThe product was extracted with EtOAc
  5. washthe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8917db0b1ef24f26b444ad16b6412605
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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