Triethylamine → Diethyl (4-chlorobenzamido)propanedioate

HRID 1840638Notes

Reaction equation

HRID 1840638 reaction equation
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 13540809Diethyl (4-chlorobenzamido)propanedioateYield 90.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.00 g of diethyl aminomalonate hydrochloride and 4.78 g of triethylamine were added to 100 ml of chloroform, and the resulting solution was stirred at the room temperature for 30 minutes. After cooling down the solution to 10° C., 4.13 g of 4-chlorobenzoylchloride was slowly added to the solution and the resulting solution was stirred at the room temperature for 2 hours. Upon the completion of the reaction, the solution was washed with 20 ml of water and 20 ml of 5% sodium bicarbonate and the organic layer was subjected to dry filtration to yield 6.70 g (90.4%) of diethyl 4-chlorobenzamidomalonate.

Workup

  1. temperatureAfter cooling down the solution to 10° C.
  2. stirringthe resulting solution was stirred at the room temperature for 2 hours
  3. customUpon the completion of the reaction
  4. washthe solution was washed with 20 ml of water and 20 ml of 5% sodium bicarbonate
  5. customto dry
  6. filtrationfiltration

Sources & evidence

ORD record
ord-517e871f3693456cb06d8b5d3fce3761
Source dataset
uspto-grants-2004_01
Patent number
US06680386B2

Reaction notes

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