Water → HCID 12223291, compound

HRID 2243184Notes

Reaction equation

HRID 2243184 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:16](I)[CH3:17].O>CN(C=O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH2:16][CH3:17])[C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 784805-Chloroisatoic anhydride

Product 1

HCID 12223291HCID 12223291, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g (5.06 mmol) of 6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione in DMF (20 ml) were carefully added 265 mg of sodium hydride (55% in mineral oil) at 0° C. This mixture was stirred for 30 min at RT and then 1.18 ml (7.59 mmol) of ethyl iodide were added. Stirring was continued for 16 h at RT, then water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The remaining residue was purified by crystallization from heptane to obtain 682 mg (60%) of 6-chloro-1-ethyl-1H-benzo[d][1,3]oxazine-2,4-dione as an off-white solid. 1HNMR (DMSO-d6, 300 MHz): δ 1.21 (t, J=7.0 Hz, 3H), 4.05 (q, J=7.0 Hz, 2H), 7.54 (d, J=9.1 Hz, 1H), 7.88 (dd, J=9.1 and 2.5 Hz, 1H), 7.96 (d, J=2.5 Hz, 1H).

Workup

  1. customat 0° C
  2. stirringStirring
  3. waitwas continued for 16 h at RT
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe remaining residue was purified by crystallization from heptane

Sources & evidence

ORD record
ord-8acaecc11c524a1e84302d097a92b518
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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