Methyl iodide → 3-Methyl-7-nitro-2-benzoxazolidinone

HRID 1975945Notes

Reaction equation

HRID 1975945 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][C:10](=[O:13])[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].[CH3:16]I>CS(C)=O.O>[CH3:16][N:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=2[O:11][C:10]1=[O:13]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 14797Potassium HydroxideHCID 21989850HCID 21989850, compound

Product 1

HCID 220000463-Methyl-7-nitro-2-benzoxazolidinoneYield 85%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

3.94 g (21.9 mmol) of 7-nitro-2-benzoxazolinone (for preparation of the latter compound, and European patent EPO189612 and references cited therein) were dissolved in 40 ml of DMSO after which 1.72 g of 85% powdered KOH (26.2 mmol) were added. While stirring and cooling (water) 3.72 g (26.2 mmol) of MeI dissolved in 6 ml of DMSO, were added dropwise over a period of 10 minutes. Stirring was continued at room temperature for 16 hrs, during the latter period an extra amount of MeI (0.5 g) was added. After the reaction was completed, the reaction mixture was diluted with water after which extraction took place with CH2Cl2. The combined organic fractions were washed with respectively water and brine after which the organic fraction was dried on MgSO4. After removal of the drying agent and evaporation of the solvent in vacuo, 4.1 g of a solid residue was left. Flash column chromatography (SiO2, eluent: CH2Cl2) of the latter yielded 3.6 g (85%) of pure 3-methyl-7-nitro-2-benzoxazolinone.

Workup

  1. additionwere added
  2. additionwere added dropwise over a period of 10 minutes
  3. stirringStirring
  4. extractionafter which extraction
  5. washThe combined organic fractions were washed with respectively water and brine after which the organic fraction
  6. customwas dried on MgSO4
  7. customAfter removal of the drying agent and evaporation of the solvent in vacuo, 4.1 g of a solid residue
  8. waitwas left

Sources & evidence

ORD record
ord-52907eb8cf5440559ed71db783ea297a
Source dataset
uspto-grants-2001_05
Patent number
US06225312B1

Reaction notes

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