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

HRID 1272251

反応式

HRID 1272251 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 220147673-(2-Nitro-2-methylpropyl)-7-nitroindole収率 131%

試薬・触媒・溶媒 2

HCID 3982-Nitropropane溶媒HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-37437d8d2cb041f294fb34755b08ad41
出典データセット
uspto-grants-2007_04
特許番号
US07208505B2

関連ノート

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