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

HRID 1255047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255047
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f68d82a9100f49e2ab1e0c6c7e5743f7
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455646B2

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