Ammonium Chloride → HCID 67549562, compound

HRID 2356739Notes

Reaction equation

HRID 2356739 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]1[NH:9][C:10]([CH2:19][CH3:20])=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:12]=1)=[O:2].[CH3:21][Mg]Br.[Cl-:24].[NH4+]>O1CCCC1>[ClH:24].[ClH:24].[OH:2][CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]1[NH:9][C:10]([CH2:19][CH3:20])=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:12]=1)[CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86593200HCID 86593200, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67549562HCID 67549562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-formylthiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole (68 mg) in tetrahydrofuran (5 ml) was added dropwise 3M methyl magnesium bromide (0.24 ml, diethyl ether solution) under argon atmosphere in an ice bath, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform:methanol=20:1) to obtain 2-[2-(1-hydroxyethyl)thiophen-3-yl]-5-ethyl-4-(3-pyridyl)-imidazole dihydrochloride (60 mg) as orange brownish powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-a986d78c380d422f8c0a1f2eb4fda7eb
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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