Dichloromethane → HCID 69921167, compound

HRID 2187952Notes

Reaction equation

HRID 2187952 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:14][NH:15][CH2:16][CH2:17]N.[Cl:19]CCl>Cl.O1CCOCC1.C(O)C>[ClH:19].[CH3:14][N:15]1[CH2:16][CH2:17][N:2]=[C:1]1[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 8014N-MethylethylenediamineHCID 81589Ethyl 4-cyanobenzoate

Product 1

HCID 69921167HCID 69921167, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1.8 g (10.3 mmol) of ethyl 4-cyanobenzoate was dissolved in a mixture of 20 ml of 4 N solution of hydrogen chloride in dioxane and 5 ml of ethanol, and the obtained solution was stirred at room temperature for 3 days. The solvent was evaporated, and the residue was washed with ethyl acetate. The obtained crude product was dissolved in 20 ml of ethanol. 1.52 g (20.6 mmol) of N-methylethylenediamine was added to the obtained solution, and they were heated under reflux for 6 hours. The solvent was evaporated, and the obtained crude product was treated with dichloromethane as the extraction solvent in an ordinary manner. The obtained crude product was dissolved in 10 ml of concentrated hydrochloric acid, and the obtained solution was stirred at 50° C. overnight. The solvent was evaporated to obtain the crude title compound.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with ethyl acetate
  3. customThe obtained crude product
  4. temperaturewere heated
  5. temperatureunder reflux for 6 hours
  6. customThe solvent was evaporated
  7. customthe obtained crude product
  8. customThe obtained crude product
  9. stirringthe obtained solution was stirred at 50° C. overnight
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5e0558a20c014f36b86eac0dfd3fcd39
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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