2-Methoxyethanol → 4-Cyano-3-(2-methoxyethoxy)aniline

HRID 393582ノート

反応式

HRID 393582 の反応式
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11](Cl)[CH:10]=1>CN1C(=O)CCC1.O>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([NH2:8])=[CH:10][C:11]=1[O:7][CH2:6][CH2:5][O:4][CH3:3])#[N:14]

参加物

6

反応物 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 887284-Amino-2-chlorobenzonitrile

生成物 1

HCID 226465404-Cyano-3-(2-methoxyethoxy)aniline収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

Sodium hydride (300 mg of an 80% suspension in mineral oil, 10 mmol) was added to 2-methoxyethanol (0.76 g, 10 mmol) in NMP (5 ml) and the mixture stirred for 15 minutes. 4-Amino-2-chlorobenzonitrile (1.5 g, 10 mmol) was added and the mixture heated at 100° C. for 5 hours. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography eluting with increasingly polar mixtures of methylene chloride/ethyl acetate to give 4-cyano-3-(2-methoxyethoxy)aniline (760 mg, 40%) as a dark yellow oil.

後処理

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent removed by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of methylene chloride/ethyl acetate

出典と根拠

ORDレコード
ord-9e8d38ce1e9944648bfcdeff6518031c
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

反応ノート

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