Aniline → Ethyl 2-(phenylamino)-2-(thiophen-2-yl)acetate

HRID 1044052ノート

反応式

HRID 1044052 の反応式
CS(O[CH:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>C(#N)C>[C:18]1([NH:17][CH:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 58556972Ethyl 2-(methylsulfonyloxy)-2-(thiophen-2-yl)acetate

生成物 1

HCID 58556958Ethyl 2-(phenylamino)-2-(thiophen-2-yl)acetate収率 77%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

Ethyl 2-(methylsulfonyloxy)-2-(thiophen-2-yl)acetate (I27) (5.7 g, 21.6 mmol), aniline (2.16 ml, 23.7 mmol) and DIPEA (4.52 ml, 25.9 mmol) were dissolved in acetonitrile (20 ml) to give a yellow solution which was heated under microwave irradiation into a sealed vial at 100° C. for 15 minutes. Conversion complete by UPLC/MS-UV. The solvent was evaporated, and the residue was dissolved in DCM and washed with water and brine, dried (Na2SO4), filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (Petroleum ether/EtOAc=85/15) to get desired compound as a solid (4.33 g, 77% yield).

後処理

  1. customto give a yellow solution which
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting crude was purified by flash chromatography (Petroleum ether/EtOAc=85/15)

出典と根拠

ORDレコード
ord-97190a87af784e6c96c3710904c02779
出典データセット
uspto-grants-2013_10
特許番号
US08563577B2

反応ノート

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