Ethylenediamine → 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

HRID 254475노트

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HRID 254475 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]#[N:11])=[C:4]([CH3:12])[CH:3]=1.[CH2:13](N)[CH2:14][NH2:15].[S]>>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH2:9][C:10]2[NH:15][CH2:14][CH2:13][N:11]=2)=[C:6]([CH3:8])[CH:7]=1

참가 물질

4

반응물 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 58951703(4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile

생성물 1

HCID 589518552-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

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온도
200 °C

실험 절차

A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%).

후처리

  1. customThe cooled reaction mixture
  2. additionwas poured onto water
  3. extractionextracted with methylene chloride
  4. washthe combined extracts washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient
  9. additioncontaining 1% conc. ammonia

출처 및 근거

ORD 기록
ord-e0abce5e19fb46938388b43c7833f41d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875645B2

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