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

HRID 1627756

反応式

HRID 1627756 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 8596263-(4-Methylbenzoyl)thiophen-2-amine収率 130.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5fc8a55d4d84a2daa06bb9f151e5ed1
出典データセット
uspto-grants-2014_07
特許番号
US08785638B2

関連ノート

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