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

HRID 131337

反応式

HRID 131337 の反応式
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

参加物

7

反応物 4

HCID 962WaterHCID 69794-Chloro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrate2 回HCID 27745842-Fluoro-5-methylbenzonitrile

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-52afe8a30ed34191ad63cd16e496adf2
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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