Water → HCID 67836131, compound

HRID 1197745Notes

Reaction equation

HRID 1197745 reaction equation
[CH:1]([C:4]1([CH3:17])[NH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)=[N:6][C:5]1=[O:16])([CH3:3])[CH3:2].C([Li])CCC.C[O:24][C:25](=O)[C:26]([N:28]([CH3:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].O>O1CCCC1>[CH:1]([C:4]1([CH3:17])[C:5](=[O:16])[NH:6][C:7]([C:9]2[C:14]([C:25](=[O:24])[C:26]([N:28]([CH3:35])[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:27])=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)=[N:8]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3707473HCID 3707473, compoundHCID 178418339ButyllithiumHCID 178423999HCID 178423999, compound

Product 1

HCID 67836131HCID 67836131, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a stirred solution of 2.5 g(0.011 mole) of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2 -yl)-5-methyl pyridine in 100ml of anhydrous tetrahydrofuran cooled to -70° C. under the presence of nitrogen was added dropwise a 9.68 ml of 2.5 molar n-butyllithium, thus maintaining temperature below -65° C. The solution was stirred at -70° C. for 3 hr and a solution 1.96 g of N-methyl-N-phenyl oxamic acid methyl ester(3.4 g, 0.016 mole) in 10 ml of anhydrous tetrahydrofuran was added dropwise while maintaining temperature below -65° C. After stirring another hour at -70° C., the solution was poured into water and extracted with methylene chloride. The combined organic phases were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography to produce 1.76 g of pale yellow solid(m.p.=153°~156° C.).

Workup

  1. temperaturethus maintaining temperature below -65° C
  2. temperaturewhile maintaining temperature below -65° C
  3. stirringAfter stirring another hour at -70° C.
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1f945fc48b5f4dc486e7109a48eaaae1
Source dataset
uspto-grants-1994_01
Patent number
US05278134

Reaction notes

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