1,3-Diethyl 2-oxopropanedioate → HCID 18369263, compound

HRID 1699725Notes

Reaction equation

HRID 1699725 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([NH2:18])=[C:10]([NH2:19])[CH:9]=2)[CH:7]=1.O=[C:21]([C:27](OCC)=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(O)C>[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:9]=[C:10]3[C:11]([NH:18][C:27](=[O:28])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:19]3)=[CH:12][C:13]=2[C:14]([F:16])([F:15])[F:17])[CH:7]=1

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 18369252HCID 18369252, compound

Product 1

HCID 18369263HCID 18369263, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-(hydroxymethyl)imidazole-1-yl)-5-trifluoromethyl-1,2-phenylenediamine (200 mg, 781 μmol) in ethanol (10 ml) was added diethyl ketomalonate (142 μl, 937 μmol), and the mixture was refluxed for 4 hours. After cooling, solvent was distilled off and the residue obtained was purified by means of silica gel column chromatography [methylene chloride-methanol (50:1→10:1)] to obtain 129 mg of the the title compound as pale yellow powder. Yield 43%.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. distillationsolvent was distilled off
  4. customthe residue obtained
  5. customwas purified by means of silica gel column chromatography [methylene chloride-methanol (50:1→10:1)]

Sources & evidence

ORD record
ord-bcbc24f5c04a403cb288222da3131fd4
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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