4-Chlorobenzoic Acid → Diethyl (4-chlorobenzamido)propanedioate

HRID 1840639Notes

Reaction equation

HRID 1840639 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:27][CH:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:27][CH:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 13540809Diethyl (4-chlorobenzamido)propanedioateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.00 g of 4-chlorobenzoic acid and 1.45 g of dicyclohexylcarbodiimide (DCC) were solved in 30 ml of tetrahydrofuran, and the resulting solution was stirred at the room temperature for 2 hours. Subsequently, 1.35 g of diethyl aminomalonate hydrochloride and 0.65 g of triethylamine were added to 20 ml of tetrahydrofuran, and after stirring for about 20 minutes, the previously prepared solution was added to the this resulting solution. The mixed solution was then stirred at the room temperature for 2 hours to complete the reaction. After filtration of the solution and concentration of the filtrate, the concentrated filtrate was diluted with 50 ml of chloroform, washed with 20 ml of water twice and subjected to dry filtration to yield 1.72 g (86%) of diethyl 4-chlorobenzamidomalonate.

Workup

  1. stirringafter stirring for about 20 minutes
  2. additionthe previously prepared solution was added to the this resulting solution
  3. stirringThe mixed solution was then stirred at the room temperature for 2 hours
  4. customthe reaction
  5. filtrationAfter filtration of the solution and concentration of the filtrate
  6. additionthe concentrated filtrate was diluted with 50 ml of chloroform
  7. washwashed with 20 ml of water twice
  8. customto dry
  9. filtrationfiltration

Sources & evidence

ORD record
ord-cd9d154f38334e0ebbe242045bdbf6b9
Source dataset
uspto-grants-2004_01
Patent number
US06680386B2

Reaction notes

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