Potassium Carbonate → HCID 45881210, compound

HRID 1042840Notes

Reaction equation

HRID 1042840 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CC(C)=O>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][CH:8]=[CH:7][C:3]2=3)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 5850963,4-Dihydro-2H-1,4-benzoxazine

Product 1

HCID 45881210HCID 45881210, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3,4-dihydro-2H-benzo[b][1.4]oxazine (0.500 g, 3.70 mmol) and potassium carbonate (2.56 g, 18.5 mmol) in acetone (25 mL) was added 1-(bromomethyl)-4-nitrobenzene (0.959 g, 4.44 mmol). The mixture was heated to reflux and stirred overnight. After 16 hrs the mixture was concentrated in vacuo, diluted with EtOAc, and washed with water and brine. The organic fraction was dried over Na2SO4, concentrated in vacuo, and the crude residue was purified by silica gel chromatography using 100% Hexanes to 30% Hexanes:EtOAc to afford 4-(4-nitrobenzyl)-3,4-dihydro-2H-benzo[b][1.4]oxazine as an orange oil. MS found: M+H+=271.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationAfter 16 hrs the mixture was concentrated in vacuo
  4. additiondiluted with EtOAc
  5. washwashed with water and brine
  6. dry with materialThe organic fraction was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customthe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8cb8396f6454d77a7d1b6af39b146f9
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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