Potassium Carbonate → HCID 22993374, compound

HRID 1167611Notes

Reaction equation

HRID 1167611 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][NH:8][C:7]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]#[N:22]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8]([CH2:20][C:21]#[N:22])[C:7]=2[CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 162444606-Methoxy-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 22993374HCID 22993374, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The compound obtained in Step D (400 mg; 2.42 mmol) is suspended in 10 ml of water. Potassium carbonate (10 eq.; 24.2 mmol; 3.35 g), tetrabutylammonium bromide (0.05 eq.; 0.12 mmol; 40 mg) and bromoacetonitrile (8 eq.; 19.37 mmol; 1.35 ml) are then added. The mixture is stirred vigorously for 12 hours at 70° C. After returning to ambient temperature, the product formed is extracted with dichloromethane. The organic phase is dried over MgSO4, filtered, and then concentrated under reduced pressure. The residue obained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/1)). The title product is obtained in the form of a solid.

Workup

  1. customAfter returning to ambient temperature
  2. customthe product formed
  3. extractionis extracted with dichloromethane
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (1/1))

Sources & evidence

ORD record
ord-21905784cea34413a1c3a2ee655438ee
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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