Potassium Carbonate → HCID 45881210, compound

HRID 503575Notes

Reaction equation

HRID 503575 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-80e616e3bf6c48ec955046e0d48e9450
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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