Acetyl chloride → HCID 20258963, compound

HRID 1583536Notes

Reaction equation

HRID 1583536 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH:12]=[N:13][NH:14][C:3]1=2.[H-].[Na+].[H][H].[C:19](Cl)(=[O:21])[CH3:20]>C1COCC1>[C:19]([N:13]1[CH:12]=[C:4]2[O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:2]([CH3:1])[C:3]2=[N:14]1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 13270065HCID 13270065, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20258963HCID 20258963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.5 g (40 mmols) of 9-methylpyrazolo[4,3-b][1,4]benzoxazine in 50 ml of absolute THF is added dropwise to a suspension of 1.8 g of sodium hydride (55-60% dispersion in oil) in 10 ml of absolute THF. After completion of evolution of hydrogen, 3.14 ml of acetyl chloride were added dropwise to the reaction mixture and the mixture was boiled under reflux for 3 hours. The solvent is removed in vacuo, the residue is taken up in water and the product is extracted at pH 7 with dichloromethane. The organic phase is evaporated and the residue is chromatographed on silica gel with ethyl acetate (dichloromethane (1:1).

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe solvent is removed in vacuo
  3. extractionthe product is extracted at pH 7 with dichloromethane
  4. customThe organic phase is evaporated
  5. customthe residue is chromatographed on silica gel with ethyl acetate (dichloromethane (1:1)

Sources & evidence

ORD record
ord-9ebf4902157647728defbb4d8214f319
Source dataset
uspto-grants-1985_11
Patent number
US04552874

Reaction notes

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