Hydrochloric Acid → HCID 178510702, compound

HRID 570832Notes

Reaction equation

HRID 570832 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]([C:15]#[N:16])=[N:8][NH:9][C:10]=1[Si](C)(C)C.[OH-].[Na+].Cl>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]([C:15]#[N:16])=[N:8][NH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68501979HCID 68501979, compound

Product 1

HCID 178510702HCID 178510702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After a solution of trimethylsilyldiazomethane in hexane (0.6 mol/L, 5 mL) was added to tetrahydrofuran (20 mL) under an argon atmosphere, to this reaction mixture was added a solution of n-butyl lithium in hexane (2.6 mol/L, 1.08 mL) in a dropwise manner over 5 minutes at −78° C., and this mixture was stirred at same temperature for 20 minutes. And then to this reaction mixture was added a solution of 2-thiophene-2-ylmethylene malononitrile (0.32 g) in tetrahydrofuran (5 mL) in a dropwise manner over 20 minutes. To this reaction mixture was added saturated aqueous ammonium chloride solution, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. This residue was washed with hexane to give 4-thiophene-2-yl-5-trimethylsilanyl-1H-pyrazole-3-carbonitrile (0.496 g). To the 4-thiophene-2-yl-5-trimethylsilanyl-1H-pyrazole-3-carbonitrile were added methanol (20 mL) and 1.0 mol/L aqueous sodium hydroxide solution (20 mL), and this mixture was heated to reflux for 2 hours. This reaction mixture was acidified (pH1) with adding 1.0 mol/L hydrochloric acid, the precipitated solid was collected by filtration. This obtained solid was washed with water, dried under reduced pressure at 50° C. to give the title compound (0.154 g).

Workup

  1. temperaturethis mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washThis obtained solid was washed with water
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-5ba23c75aaae4eeb9b1e0e55ad0eec79
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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