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

HRID 131380

反応式

HRID 131380 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2c4b8a4f82994450bcaa96a83066b968
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

読み込み中…