Triethylamine → HCID 58658936, compound

HRID 2234822Notes

Reaction equation

HRID 2234822 reaction equation
[NH2:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[CH:17]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>ClCCl>[C:8]([CH:2]([NH:1][C:23]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:24])[C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 288716Ethyl 2-amino-2-cyanoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 58658936HCID 58658936, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 18.3 g (143 mmol) of ethyl amino(cyano)acetate in 500 mL of anhydrous dichloromethane were added 30 mL (214 mmol) of triethylamine and 23 mL (171 mmol) of cyclohexanecarbonyl chloride, and the mixture was stirred for 3 hours at 0° C. Then, saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was washed with water and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was treated with ethyl acetate to give the solid substance. The obtained solid substance was collected and the filtrate was removed under reduced pressure. The obtained residue was treated with ethyl acetate to give solid substance. This treatment was further repeated. The filtrate was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1) to give crude crystalline. The obtained crude crystalline was washed with ether and combined with the above all solid products to give 24.3 g (71%) of the title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water and saturated saline solution
  3. dry with materialdried over with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated with ethyl acetate
  6. customto give the solid substance
  7. customThe obtained solid substance was collected
  8. customthe filtrate was removed under reduced pressure
  9. additionThe obtained residue was treated with ethyl acetate
  10. customto give solid substance
  11. customThe filtrate was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1)
  12. customto give crude crystalline
  13. customThe obtained crude
  14. washcrystalline was washed with ether

Sources & evidence

ORD record
ord-df5573a3867c49de83388577fb158312
Source dataset
uspto-grants-2010_05
Patent number
US07713972B2

Reaction notes

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