Water → 2-(4-Chloro-2-nitro-phenylamino)-5-methyl-benzonitrile

HRID 131337

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HRID 131337 반응식
F[C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1.O.[OH-].[Li+].O>CS(C)=O.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:2]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=2[C:4]#[N:5])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 69794-Chloro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrate2회HCID 27745842-Fluoro-5-methylbenzonitrile

생성물 1

HCID 586258892-(4-Chloro-2-nitro-phenylamino)-5-methyl-benzonitrile수율 38.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매2회

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온도
70 °C

실험 절차

Heat a solution of 2-fluoro-5-methyl-benzonitrile (2.0 g, 14.80 mmol) with 4-chloro-2-nitro-phenylamine (2.5 g, 14.80 mmol) and lithium hydroxide monohydrate (1.24 g, 29.60 mmol) in DMSO (30 ml) to 55° C. for 14 hours. Add an additional 0.61 g (14.80 mmol) of lithium hydroxide monohydrate, and increase heating to 70° C., continue for another 14 hours. Cool the reaction to ambient temperature and pour into a mixture of 100 ml water and 200 ml ethyl acetate. Extract with three 200 ml portions of ethyl acetate. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a step gradient starting with 90% hexanes: 10% ethyl acetate and going to 40% hexanes: 60% ethyl acetate to obtain 1.63 g (5.67 mmol, 38% yield) of the title compound as a red-orange amorphous solid: Mass Spectrum (m/e): 288 (M+1).

후처리

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

출처 및 근거

ORD 기록
ord-52afe8a30ed34191ad63cd16e496adf2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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