1-Bromo-2-Chloroethane → HCID 66642902, compound

HRID 869248Notes

Reaction equation

HRID 869248 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][Cl:24].C(=O)([O-])O.[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:24][CH2:23][CH2:22][N:8]1[C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:11][CH2:10][C:9]1=[O:12]

Participants

7

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 66642902HCID 66642902, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 7-nitro-2H-1,4-benzoxazine-3(4H)-one (2.0 g), benzyltriethylammonium chloride (470 mg), potassium carbonate (4.27 g) and acetonitrile (60 mL), 1-bromo-2-chloroethane (1.28 mL) was added and stirred at 75° C. for 3 hours. After the reaction liquid was cooled, saturated aqueous sodium hydrogen carbonate was added, and the reaction liquid was extracted with ethyl acetate and the extract was washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to give 4-(2-chloroethyl)-7-nitro-2H-1,4-benzoxazine-3(4H)-one (1.92 g) as a yellow powder.

Workup

  1. additionwas added
  2. customAfter the reaction liquid
  3. temperaturewas cooled
  4. customthe reaction liquid
  5. extractionwas extracted with ethyl acetate
  6. washthe extract was washed with saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-0fced1b9520e49d5af28176bb15e29b2
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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