Water → Diethyl 2-(3-methylbenzamido)malonate

HRID 1626016Notes

Reaction equation

HRID 1626016 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:13])[CH:6]([NH2:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].C(N(CC)CC)C.[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26].O>ClCCl>[CH2:10]([O:9][C:7](=[O:8])[CH:6]([NH:12][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([CH3:21])[CH:23]=1)[C:5]([O:4][CH2:2][CH3:3])=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 743753-Methylbenzoyl chlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 33240476Diethyl 2-(3-methylbenzamido)malonateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

41.1 g of aminomalonic acid diethyl ester hydrochloride were dissolved in 200 ml of dichloromethane, and 80.7 ml of triethylamine were added with cooling in an ice bath. A solution of 30 g of 3-methyl-benzoyl chloride in 200 ml of dichloromethane was slowly added dropwise. After 2 h at 0° C., 100 ml of water were added dropwise. The phases were separated, and the aqueous phase was extracted with 100 ml of dichloromethane. The combined organic phases were dried with sodium sulfate, filtered and evaporated to give 54 g of the crude title compound.

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with 100 ml of dichloromethane
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3f1c12cb86f948c7b0532b604da33f1f
Source dataset
uspto-grants-2014_07
Patent number
US08785439B2

Reaction notes

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