Dimethyl Sulfoxide → 3-Methyl-7-nitro-2-benzoxazolidinone

HRID 323602Notes

Reaction equation

HRID 323602 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]S(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

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 14797Potassium HydroxideHCID 21989850HCID 21989850, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.94 g (21.9 mmol) of 7-nitro-2-benzoxazolidinone (for preparation of the latter compound, see EP 0189612 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 Mel 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 Mel (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 water and brine respectively, 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-benzoxazolidinone.

Workup

  1. additionwere added
  2. additionwere added dropwise over a period of 10 minutes
  3. stirringStirring
  4. additionan extra amount of Mel (0.5 g) was added
  5. extractionafter which extraction
  6. washThe combined organic fractions were washed with water and brine respectively
  7. customafter which the organic fraction was dried on MgSO4
  8. customAfter removal of the drying agent and evaporation of the solvent in vacuo, 4.1 g of a solid residue
  9. waitwas left

Sources & evidence

ORD record
ord-70e4779ae45840b2b2f61e0c83375a6a
Source dataset
uspto-grants-2001_04
Patent number
US06214829B1

Reaction notes

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