Lithium Hydroxide → 2-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

HRID 131330ノート

反応式

HRID 131330 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[F:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH:19]=1

参加物

6

反応物 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 679672,4-DifluoronitrobenzeneHCID 210934632-Amino-5-isopropylbenzonitrile

生成物 1

HCID 586259572-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile収率 16.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Heat a solution of 2-amino-5-isopropyl-benzonitrile (1.21 g, 7.55 mmol) with 2,4-difluoro-1-nitro-benzene (1.20 g, 7.55 mmol) and lithium hydroxide (0.54 g, 22.66 mmol) in DMSO (15 ml) to 70° C. for 18 hours. Cool the reaction to ambient temperature and then pour into approximately 200 ml of ice water and stir for one hour. The title compound precipitates and is colleted by filtration. Purify the solid via flash chromatography eluting with a 95% hexanes: 5% ethyl acetate mobile phase to obtain 0.372 g (1.24 mmol, 16% yield) of the title compound as an orange amorphous solid: Mass Spectrum (m/e): 298 (M−1).

後処理

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. customThe title compound precipitates
  4. filtrationis colleted by filtration
  5. customPurify the solid via flash chromatography
  6. washeluting with a 95% hexanes

出典と根拠

ORDレコード
ord-c4491ebbc188498abc9e2e87309ba20e
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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