Ethyl Acetate → 2-(4,5-Difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

HRID 131335

反応式

HRID 131335 の反応式
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([NH2:22])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[F:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([NH:22][C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[C:4]#[N:5])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 1571514,5-Difluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

生成物 1

HCID 586259642-(4,5-Difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile収率 50.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Heat a solution of 2-fluoro-5-trifluoromethyl-benzonitrile (1.0 g, 5.74 mmol) with 4,5-difluoro-2-nitro-phenylamine (1.09 g, 5.74 mmol) and lithium hydroxide monohydrate (0.48 g, 11.49 mmol) in DMSO (12 ml) to 55° C. for 16 hours. Cool the reaction to ambient temperature and then add approximately 150 ml of ice water and stir the mixture for one hour. Extract with three 200 ml portions of dichloromethane. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a linear gradient starting with 100% hexanes and going to 70% hexanes: 30% ethyl acetate to obtain 0.995 g (2.90 mmol, 50% yield) of the title compound as a yellow amorphous solid: Mass Spectrum (m/e): 344 (M+1).

後処理

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. extractionExtract with three 200 ml portions of dichloromethane
  4. dry with materialCombine organic layers, dry over sodium sulfate
  5. customevaporate solvent
  6. customPurify the residue via flash chromatography
  7. washeluting with a linear gradient

出典と根拠

ORDレコード
ord-9f2ac96a8a4a4b6999fcc549bb9bedd3
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…