Ethyl iodoacetate → Ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate

HRID 572600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572600
[N:1]1([C:7](=[S:11])[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=O.CCN(C(C)C)C(C)C.I[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(#N)C>[C:9]([C:8]1[C:15]([C:14]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:13]=2[Cl:12])=[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[S:11][C:7]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)#[N:10]

Komponenten

6

Edukt 4

HCID 12183Ethyl iodoacetateHCID 666452,4-Dichlorobenzoyl chlorideHCID 81531Diisopropylethylamine2×HCID 451589413-Morpholin-4-yl-3-thioxopropanenitrile

Produkt 1

HCID 44155898Ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 3-morpholin-4-yl-3-thioxopropanenitrile (0.150 g, 0.88 mmol) in anhydrous ACN (1.2 mL) was cooled to 0° C. To this cooled solution was added of 2,4-dichlorobenzoyl chloride (0.149 mL, 1.06 mmol) and DIPEA (0.161 mL, 0.93 mmol). The mixture was allowed to stir at rt under nitrogen for 15 min before ethyl iodoacetate (0.10 mL, 0.93 mmol) and DIPEA (0.161 mL, 0.93 mmol) were added. The reaction mixture was subjected to MWI at 140° C. for 10 min. The mixture was allowed to cool and was concentrated. The residue was purified by column chromatography to give ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate (78) (0.1 g, 28%). LCMS: (AA) ES+ 411.09. 1H NMR (400 MHz, CDCl3) δ: 7.49 d, 1H), 7.33 (dd, 1H), 7.20 (d, 1H), 4.08-4.16 (m, 2H), 3.85-3.89 (m, 4H), 3.63-3.66 (m, 4H) and 1.12 (t, 3H).

Aufarbeitung

  1. additionwere added
  2. temperatureto cool
  3. concentrationwas concentrated
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2a1af50d26f54388abc6e7224476bd10
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029411B2

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