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

HRID 131330

반응식

HRID 131330 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4491ebbc188498abc9e2e87309ba20e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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