1,3-Diethyl 2-oxopropanedioate → HCID 18369207, compound

HRID 1699731Notes

Reaction equation

HRID 1699731 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:8][C:9]([NH2:13])=[C:10]([NH2:12])[CH:11]=1.O=[C:19]([C:25](OCC)=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[C:10]2[C:9]([NH:13][C:25](=[O:26])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12]2)=[CH:8][C:7]=1[C:14]([F:15])([F:16])[F:17]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 57009865HCID 57009865, compound

Product 1

HCID 18369207HCID 18369207, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-imidazolyl-4-trifluoromethyl-1,2-phenylenediamine (303 mg, 1.25 mmol) in ethanol (50 ml) was added diethyl ketomalonate (210 μl, 1.38 mmol) at room temperature, and the mixture was refluxed for 6 hours. The reaction mixture. was concentrated to around half volume under reduced pressure, then the precipitate was collected by filtration and washed with cold ethanol. The filtrate was distilled off under reduced pressure, small quantity of mixed solution of ethyl acetate-diisopropyl ether was added to the residue obtained and the precipitate was collected by filtration to obtain 148 mg of the title compound as pale yellowish brown powder. Yield 34%.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. concentrationwas concentrated to around half volume under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with cold ethanol
  5. distillationThe filtrate was distilled off under reduced pressure, small quantity of mixed solution of ethyl acetate-diisopropyl ether
  6. additionwas added to the residue
  7. customobtained
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-634cc3ed38d4450b83da70cc7c0cbaea
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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