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

HRID 1975945노트

반응식

HRID 1975945 반응식
[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]

참가 물질

6

반응물 3

HCID 6328Methyl iodide2회HCID 14797Potassium HydroxideHCID 21989850HCID 21989850, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52907eb8cf5440559ed71db783ea297a
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225312B1

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