Iodoethane → HCID 10668213, compound

HRID 266675Notes

Reaction equation

HRID 266675 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[O:3][CH:2]=1.[H-].[Na+].[CH2:14]([I:16])[CH3:15]>C1COCC1>[CH2:6]([N:1]([C:15]1[CH:10]=[CH:9][CH:8]=[CH:7][C:14]=1[I:16])[C:2]1[O:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:1]=1)[CH3:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10920656HCID 10920656, compound

Product 1

HCID 10668213HCID 10668213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-Iodo-phenyl)-amino]-benzo[d][1,3]oxazin-4-one (0.308 g, 0.00085 mol) was dissolved in THF (5 mL), and NaH (0.040 g, 0.0010 mol) was added. The reaction was stirred for 30 minutes and ethyl iodide (0.312 g, 0.0020 mol) was added. The reaction was heated to 60° C. and stirred for 24 hours under a nitrogen atmosphere. The reaction mixture was partitioned between H2O (200 mL) and ethyl acetate (200 mL). The ethyl acetate layer was dried (MgSO4), filtered, and concentrated in vacuo. The crude residue was chromatographed on a silica gel column eluted with petroleum ether:ethyl acetate (7:3). The product was recrystallized from ether/hexanes to produce the target compound as a white solid, mp 129°-130° C.).

Workup

  1. stirringstirred for 24 hours under a nitrogen atmosphere
  2. customThe reaction mixture was partitioned between H2O (200 mL) and ethyl acetate (200 mL)
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was chromatographed on a silica gel column
  7. washeluted with petroleum ether:ethyl acetate (7:3)
  8. customThe product was recrystallized from ether/hexanes

Sources & evidence

ORD record
ord-7e21170da6b84f7386e3de953fc70b9e
Source dataset
uspto-grants-1997_07
Patent number
US05652237

Reaction notes

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