Dichloromethane → Diethyl p-toluoylaminomalonate

HRID 857207Notes

Reaction equation

HRID 857207 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(Cl)Cl.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>C(N(CC)CC)C>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23]([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:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 134054-Methylbenzoyl ChlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 17447783Diethyl p-toluoylaminomalonateYield 91.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Diethyl aminomalonate hydrochloride (20.5 g) was suspended into 180 ml of methylene chloride, and 29.4 g of triethylamine was added while cooling with ice-cold water. After 30-minute-stirring, 15 g of p-toluoyl chloride was added dropwise, and the mixture was stirred for 24 hours at room temperature. The reaction solution was washed with water, dilute hydrochloric acid, and water, dried over anhydrous magnesium sulfate and concentrated. To the residue was added isopropyl ether, and the resultant crystals were collected by filtration and dried to provide 25.9 g of the objective compound as white crystal. M.p. 101-102° C.

Workup

  1. additionwas added
  2. temperaturewhile cooling with ice-cold water
  3. stirringthe mixture was stirred for 24 hours at room temperature
  4. washThe reaction solution was washed with water, dilute hydrochloric acid, and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. additionTo the residue was added isopropyl ether
  8. filtrationthe resultant crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-98bd880f558a4fcca0e0ecf3e3922321
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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