2-Cyanoacetyl chloride → HCID 178435091, compound

HRID 2404530Notes

Reaction equation

HRID 2404530 reaction equation
[F:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[NH:7][NH2:8].[C:11]([CH2:13][C:14](Cl)=[O:15])#[N:12]>O1CCCC1>[NH2:12][C:11]1[N:7]([C:6]2[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=2[F:1])[N:8]=[C:14]([OH:15])[CH:13]=1

Participants

4

Reactant 2

HCID 110515942-Cyanoacetyl chlorideHCID 68487761HCID 68487761, compound

Product 1

HCID 178435091HCID 178435091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, the obtained hydrazine derivative was dissolved in 50 mL of tetrahydrofuran, and to this solution, 5.1 g of cyanoacetyl chloride was added, followed by stirring at room temperature for 2 hours. Then, the solvent was distilled off under reduced pressure, the residue was dissolved in 50 mL of 1-propanol, and 3.1 g of methanesulfonic acid was added, followed by reflux with heating for 3 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, followed by neutralization with sodium hydrogen carbonate to a pH of 7, and extraction with ethyl acetate was carried out. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 5.5 g of 5-amino-1-(2-fluoro-4-methyl-5-methylthiophenyl)-3-hydroxypyrazole in the form of yellow crystals (melting point: 230-232° C.).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 50 mL of 1-propanol
  3. addition3.1 g of methanesulfonic acid was added
  4. temperatureby reflux
  5. temperaturewith heating for 3 hours
  6. temperatureAfter cooling to room temperature
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionfollowed by neutralization with sodium hydrogen carbonate to a pH of 7, and extraction with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d001b37b0c2a43629c65c4c00f0c92f5
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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