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

HRID 1272251

반응식

HRID 1272251 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-37437d8d2cb041f294fb34755b08ad41
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208505B2

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