1,2-Dichloroethane → Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate

HRID 1776491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776491
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18](=[O:23])[CH2:19][C:20](O)=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:20](=[O:21])[CH2:19][C:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:23])=[CH:5][CH:4]=1

Komponenten

7

Edukt 3

HCID 111,2-DichloroethaneHCID 660384-(Methylthio)anilineHCID 1816593-(Benzyloxy)-3-oxopropanoic acid

Produkt 1

HCID 86679443Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(methylthio)aniline (500 mg, 3.59 mmol), 3-(benzyloxy)-3-oxopropanoic acid (1046 mg, 5.39 mmol), DMAP (527 mg, 4.31 mmol), and EDC (1377 mg, 7.18 mmol) were dissolved in DMF (7 ml). The reaction was stirred at RT for 4 hours. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate (520 mg, 45.9% yield).

Aufarbeitung

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0ea2da153e1248f7884524b53c5a4582
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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