Dimethyl Sulfate → 3-(2-Nitro-2-methylpropyl)-7-nitroindole

HRID 1072623

반응식

HRID 1072623 반응식
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N+:14]([O-:16])=[O:15])[C:8]=2[NH:7][CH:6]=1)C.COS(OC)(=O)=O.C[O-].[Na+]>[N+](C(C)C)([O-])=O.CO>[N+:14]([C:13]([CH3:8])([CH3:12])[CH2:4][C:5]1[C:9]2[C:8](=[C:13]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1)([O-:16])=[O:15]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 15451Indole, 3-((dimethylamino)methyl)-7-nitro-HCID 10942334Sodium Methoxide

생성물 1

HCID 220147673-(2-Nitro-2-methylpropyl)-7-nitroindole수율 131%

시약·촉매·용매 2

HCID 3982-Nitropropane용매HCID 887Methanol용매

실험 절차

The 7-nitrogramine salt (2.0 g, 5.8 mmol) is suspended in a mixture of 2-nitropropane (9.5 mL) and methanol (9.5 mL). Dimethylsulfate (1.09 mL, 11.5 mmol) is added dropwise via syringe, and the resulting yellow solution is stirred at room temperature for 5 minutes. Sodium methoxide (0.62 g, 11.5 mmol) is then added in one portion, and the mixture is stirred overnight at room temperature. The reaction is quenched by addition of saturated NH4Cl solution and ethyl acetate. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are washed with brine, and dried over Na2SO4 to give 1.0 g of 3-(2-nitro-2-methylpropyl)-7-nitroindole (69%).

후처리

  1. stirringthe mixture is stirred overnight at room temperature
  2. customThe reaction is quenched by addition of saturated NH4Cl solution and ethyl acetate
  3. extractionThe aqueous layer is extracted with ethyl acetate
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-5ba55724ebce42ff82d349d65ee36bd6
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911463B2

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