Methyl iodide → 7-Fluoro-2-methylisatoicanhydride

HRID 542796Notes

Reaction equation

HRID 542796 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:16]I>CC(N(C)C)=O>[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=[O:10])[N:9]([CH3:16])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 103302747-Fluoro-2-methylisatoicanhydride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of 7-fluoro-1H-3,1-benzoxazine-2,4-dione (9.0 g) in dimethylacetamide (100 ml) at 18.5° was treated portionwise with sodium hydride (80% dispersion in mineral oil, 1.65 ) during 10 minutes. The mixture was stirred for a further 75 minutes. Methyl iodide (7.81 g) was then added dropwise to the stirred mixture during 5 minutes and the mixture was stirred for a further 18.5 hours at ambient temperature. Solvent (60 ml) was removed by distillation in vacuo. The residue was cooled to 3° and poured into ice-water. The resulting precipitate was collected, dried in vacuo and recrystallised from dichloromethane to give 7-fluoro-1-methyl-1H-3,1-benzoxazine-2,4-dione m.p. 158°-159.5°.

Workup

  1. stirringthe mixture was stirred for a further 18.5 hours at ambient temperature
  2. customSolvent (60 ml) was removed by distillation in vacuo
  3. temperatureThe residue was cooled to 3°
  4. additionpoured into ice-water
  5. customThe resulting precipitate was collected
  6. customdried in vacuo
  7. customrecrystallised from dichloromethane

Sources & evidence

ORD record
ord-ef26692064e547e8a0e4e3b85480da65
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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