Triethylamine → diethyl 2-(methylcarbamoylamino)propanedioate

HRID 1639168Notes

Reaction equation

HRID 1639168 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.[CH3:21][N:22]=[C:23]=[O:24]>O1CCCC1CO>[CH3:21][NH:22][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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 295908diethyl 2-(methylcarbamoylamino)propanedioateYield 91.1%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of diethyl 2-aminomalonate hydrochloride (4.2 g) and triethylamine (2.12 g) in tetrahydrofuran-methanol is added dropwise methyl isocyanate (1.25 g) at 0° to 5° C., and the mixture is stirred at room temperature for 5 hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added chloroform. The organic layer is separated, washed, dried and then concentrated. The residue is recrystallized from chloroform-isopropyl ether to give diethyl 2-[(methylcarbamoyl)amino]malonate (4.2 g), m.p. 139° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionto the residue is added chloroform
  3. customThe organic layer is separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is recrystallized from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-d340a365e4c642a1a978212183d486bc
Source dataset
uspto-grants-1989_11
Patent number
US04882447

Reaction notes

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