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

HRID 1255047노트

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HRID 1255047 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f68d82a9100f49e2ab1e0c6c7e5743f7
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455646B2

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