2,4-Difluoronitrobenzene → 2-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile

HRID 131380

반응식

HRID 131380 반응식
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]#[N:19].O.[OH-].[Li+]>CS(C)=O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:18]#[N:19])[CH:7]=1

참가 물질

5

반응물 3

HCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 7366072-Aminothiophene-3-carbonitrile

생성물 1

HCID 692118502-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile수율 45%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Combine 2,4-difluoro-1-nitro-benzene (5.24 g, 32.94 mmol), 2-aminothiophene-3-carbonitrile (4.09 g, 32.94 mmol), and DMSO (30.0 ml). Add lithium hydroxide monohydrate (2.76 g, 65.88 mmol) all at once and then stir the mixture at 55° for 22 hours. Cool the mixture to ambient temperature and then pour it onto ice chips. Extract with ethyl acetate and then wash (brine), dry (sodium sulfate), and evaporate the organic to residue. Purify the residue on silica gel using hexanes/dichloromethane (35:65) to give 3.89 g (45%) of the title compound as a red solid: mass spectrum (ion spray): m/z=262.0 (M−1).

후처리

  1. additionpour it onto ice chips
  2. extractionExtract with ethyl acetate
  3. washwash (brine)
  4. dry with materialdry (sodium sulfate)
  5. customevaporate the organic to residue
  6. customPurify the residue on silica gel

출처 및 근거

ORD 기록
ord-2c4b8a4f82994450bcaa96a83066b968
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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