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

HRID 422016노트

반응식

HRID 422016 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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+),

후처리

  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

출처 및 근거

ORD 기록
ord-4a5f5d18ba69451184fc11a4f0efc89a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101608B2

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