Formaldehyde → HCID 67547462, compound

HRID 2356711Notes

Reaction equation

HRID 2356711 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][CH:9]=[C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)=[CH:4][CH:3]=1.C=O.[C:20](=O)([O-])[O-:21].[K+].[K+].C(O)(C)C>O.CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9]([CH2:20][OH:21])=[C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 178477976HCID 178477976, compound

Product 1

HCID 67547462HCID 67547462, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(5-chlorothiophen-2-yl)-4-(3-pyridyl) imidazole (1.07 g), 35% formalin aqueous solution (35 ml), potassium carbonate (1.70 g), isopropanol (30 ml) and N,N-dimethyl-formamide (10 ml) was stirred at 90° C. for 2 hours. After cooling, water was added to the mixture and precipitated solid was collected by filtration. The solid was dissolved in methanol and, after removing insolubles by filtration, the solvent was removed under reduced pressure. The resulting residue was triturated with ethyl acetate to obtain 2-(5-chlorothiophen-2-yl)-5-hydroxymethyl-4-(3-pyridyl)imidazole (519 mg) as colorless powder.

Workup

  1. temperatureAfter cooling
  2. customprecipitated solid
  3. filtrationwas collected by filtration
  4. dissolutionThe solid was dissolved in methanol
  5. customafter removing insolubles
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe resulting residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-e2cecadca6524bf8a184547aa34ac465
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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