Triethylamine → HCID 67865961, compound

HRID 892424Notes

Reaction equation

HRID 892424 reaction equation
[CH2:1]([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])[CH3:2].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1.C([N:21](CC)CC)C>C(Cl)Cl>[CH2:1]([CH:3]([C:7]([NH2:21])=[O:8])[C:4]([NH:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 67865961HCID 67865961, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a stirred, cooled (0° C.) solution of 2.13 mL (0.017 mol) of ethyl malonyl chloride in 10 mL of methylene chloride under nitrogen was added dropwise a solution of 2.03 mL (0.017 mol) of m-anisidine in 10 mL of methylene chloride over a half-hour period. After the addition the reaction mixture was allowed to warm to room temperature and stir for 2 h. The reaction mixture was cooled to 0° C. and a solution of 2.36 mL (0.017 mol) of triethylamine in 10 mL of methylene chloride was added dropwise over 2 h. Additional methylene chloride was added to keep the slurry of salts stirring efficiently. After the addition the reaction mixture was kept cold by placing it in the freezer. After 12 h the reaction was allowed to warm to room temperature and was immediately washed with water three times to remove the salts. The organic layer was dried over magnesium sulfate and filtered. Removal of solvent gave a crude oil. Purification by flash-chromatography (silica gel, 25% ethyl acetate/hexane eluent) afforded 2.5 g (64% yield) of ethyl N-3-methoxyphenylmalonamide as a red oil.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. stirringstirring efficiently
  4. additionAfter the addition the reaction mixture
  5. waitAfter 12 h the reaction was allowed
  6. temperatureto warm to room temperature
  7. washwas immediately washed with water three times
  8. customto remove the salts
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. customRemoval of solvent
  12. customgave a crude oil
  13. customPurification by flash-chromatography (silica gel, 25% ethyl acetate/hexane eluent)

Sources & evidence

ORD record
ord-7050a8e5731c41e98d305dcbefebd238
Source dataset
uspto-grants-1992_06
Patent number
US05118681

Reaction notes

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