Sodium Bicarbonate → HCID 68264843, compound

HRID 877483Notes

Reaction equation

HRID 877483 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9]N=C1CCCC1=O.[C:17]([O-:20])(O)=O.[Na+]>CC#N.OS(O)(=O)=O>[Cl:1][C:2]1[C:3]2[NH:9][C:3]3[C:17](=[O:20])[CH2:6][CH2:7][C:2]=3[C:4]=2[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86676827HCID 86676827, compound

Product 1

HCID 68264843HCID 68264843, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-(2,4-dichlorophenyl)hydrazono)cyclopentanone (2.2 g, 8.59 mmol) in MeCN (10 mL), H2SO4 (1.4 mL, 1.8M solution) was added and the mixture stirred at 80° C. for 16 h. The reaction mixture was cooled to room temperature, basified with saturated NaHCO3 and extracted with EtOAc (3×30 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude title compound as an off-white solid (800 mg) which was used in the next step without purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4016252e89b3443d8ad0c73f244614ca
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

Loading…