Phenyl chloroformate → HCID 69434247, compound

HRID 970292Notes

Reaction equation

HRID 970292 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C([Li])CCC.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>O1CCCC1.CCCCCC>[O:1]1[CH2:6][C:5](=[O:7])[N:4]([C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-oneHCID 178418339Butyllithium

Product 1

HCID 69434247HCID 69434247, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under an anhydrous atmosphere, a solution of 10 mmol of 2H-pyrido[3,2-b][1,4]oxazin-3-one in 50 ml of tetrahydrofuran is cooled to −78° C. At that temperature, 11 mmol of a 1.6M solution of n-butyllithium in hexane are added dropwise. After 30 minutes' contact at −78° C., 11 mmol of phenyl chloroformate are added dropwise and stirring is maintained for a further 2 hours. After returning to ambient temperature, the solution is hydrolysed and then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated. After purification by chromatography on silica gel (petroleum ether/ethyl acetate: 8/2), the expected product is isolated.

Workup

  1. temperatureis maintained for a further 2 hours
  2. customAfter returning to ambient temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customAfter purification by chromatography on silica gel (petroleum ether/ethyl acetate: 8/2)

Sources & evidence

ORD record
ord-7142c28f697543b0b42615f0604bb819
Source dataset
uspto-grants-2007_12
Patent number
US07312213B2

Reaction notes

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