Triethylamine → 3-(4-Methylbenzoyl)thiophen-2-amine

HRID 1627756

반응식

HRID 1627756 반응식
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.[S:13]1CC(O)S[CH2:15][CH:14]1O.C(N(CC)CC)C>C(O)C>[NH2:10][C:9]1[S:13][CH:14]=[CH:15][C:8]=1[C:6]([C:5]1[CH:11]=[CH:12][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:7]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 983301,4-Dithiane-2,5-diolHCID 5225133-(4-Methylphenyl)-3-oxopropanenitrile

생성물 1

HCID 8596263-(4-Methylbenzoyl)thiophen-2-amine수율 130.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

To a suspension of 4-methylbenzoylacetonitrile (0.325 g; 2.042 mmol) and p-dithiane-2,5-diol (0.155 g; 1.018 mmol) in ethanol (4.3 mL) cooled at 0° C. was added triethylamine (0.283 mL; 2.042 mmol). After 10 min at room temperature, the reaction mixture was heated under reflux for 2 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulphatesulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-25%) in heptane to afford the title compound (0.288 g; 65%) as a yellow solid.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulphatesulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-25%) in heptane

출처 및 근거

ORD 기록
ord-d5fc8a55d4d84a2daa06bb9f151e5ed1
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785638B2

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