Dimethyl malonate → 2-[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-malonic acid dimethyl ester

HRID 422016ノート

反応式

HRID 422016 の反応式
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].F[C:13]1[C:14]([N+:29]([O-:31])=[O:30])=[C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[CH:16]=[CH:17][CH:18]=1.[NH4+].[Cl-]>CS(C)=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:14]=1[N+:29]([O-:31])=[O:30])[C:3]([O:10][CH3:11])=[O:9]

参加物

6

反応物 4

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59804315(3-Fluoro-2-nitro-phenyl)-(3-nitro-phenyl)-amine

生成物 1

HCID 866231752-[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-malonic acid dimethyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a suspension of NaH (60% dispersion in mineral oil, 0.26 g, 11 mmol) in DMSO (30 ml) is added dimethyl malonate (1.43 g, 11 mmol) slowly. The reaction is stirred at room temperature for 1 hour. After that, a solution of (3-fluoro-2-nitro-phenyl)-(3-nitro-phenyl)-amine (1.0 g, 3.6 mmol) in DMSO (5 ml) is added. The reaction is brought to 80° C. and stirred for 20 hours. It is poured into saturated NH4Cl and extracted with ethyl acetate (30 ml×3). The organic layers are combined, washed with water, brine and dried with Na2SO4. The desired compound is obtained after purification of the residue by flash column chromatography (silica gel, eluted by hexa-nes-ethyl acetate): LC-MS: 390.0 (MH+),

後処理

  1. customis brought to 80° C.
  2. stirringstirred for 20 hours
  3. extractionextracted with ethyl acetate (30 ml×3)
  4. washwashed with water, brine
  5. dry with materialdried with Na2SO4

出典と根拠

ORDレコード
ord-4a5f5d18ba69451184fc11a4f0efc89a
出典データセット
uspto-grants-2012_01
特許番号
US08101608B2

反応ノート

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