Water → HCID 19104666, compound

HRID 1197744Notes

Reaction equation

HRID 1197744 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]([CH3:30])[CH3:29])=[O:27].O>O1CCCC1>[CH3:29][N:28]([C:26](=[O:27])[C:25]([C:14]1[C:9]([C:7]2[NH:6][C:5](=[O:16])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:17])[N:8]=2)=[N:10][CH:11]=[C:12]([CH3:15])[CH:13]=1)=[O:24])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 13280608Methyl (dimethylamino)(oxo)acetateHCID 178418339ButyllithiumHCID 178423999HCID 178423999, compound

Product 1

HCID 19104666HCID 19104666, compoundYield 46%

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 100 ml of dry tetrahydrofuran cooled to -70° C. under the presence of nitrogen was added dropwise a 9.68 ml of 2.5 molar n-butyllithium, thereby temperature was maintained below -65° C. The solution was stirred at -70° C. for 3 hours and a solution 1.96 g of N,N-dimethyl oxamic acid methyl ester(0.015 mole) in 10 ml of anhydrous tetrahydrofuran was added dropwise while maintaining the 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 magnesium sulfate, and evaporated under reduced pressure. Trituration of the residue with diethyl ether affored a crude solid which was recrystallized from a mixture of diethyl ether and methylene chloride to yield 1.67 g of a white solid (m.p=180°-182° C.).

Workup

  1. temperaturetemperature was maintained below -65° C
  2. temperaturewhile maintaining the 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 magnesium sulfate
  6. customevaporated under reduced pressure
  7. customwas recrystallized from a mixture of diethyl ether and methylene chloride

Sources & evidence

ORD record
ord-90376fa523c24266a538b2be35954a68
Source dataset
uspto-grants-1994_01
Patent number
US05278134

Reaction notes

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