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

HRID 393582노트

반응식

HRID 393582 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 226465404-Cyano-3-(2-methoxyethoxy)aniline수율 40%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e8d38ce1e9944648bfcdeff6518031c
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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