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

HRID 77014ノート

反応式

HRID 77014 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 (I87) (5.7 g, 21.6 mmol), aniline (2.16 mL, 23.7 mmol) and DIPEA (4.52 mL, 25.9 mmol) are dissolved in acetonitrile (20 mL) to give a yellow solution which is heated under microwave irradiation into a sealed vial at 100° C. for 15 minutes. Conversion complete by UPLC/MS-UV. Solvent is evaporated and the residue is dissolved in DCM and washed with water and brine, dried (Na2SO4), filtered and evaporated to dryness. The resulting crude is purified by flash chromatography (Petroleum ether/EtOAc=85/15) to get desired compound as a yellow solid (4.33 g, 77% yield).

後処理

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

出典と根拠

ORDレコード
ord-81c81ccc68e24609b1e21d645cc0f8ee
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

反応ノート

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