Cyanoacetic acid → HCID 69607371, Verbindung

HRID 1244150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244150
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].[CH2:7]([O:9][C:10]([C:12]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]=[CH2:26])=[CH:19][CH:18]=2)=[C:15]([CH3:27])[S:14][C:13]=1[NH2:28])=[O:11])[CH3:8].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:7]([O:9][C:10]([C:12]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]=[CH2:26])=[CH:19][CH:18]=2)=[C:15]([CH3:27])[S:14][C:13]=1[NH:28][C:4](=[O:5])[CH2:3][C:1]#[N:2])=[O:11])[CH3:8]

Komponenten

5

Edukt 3

HCID 9740Cyanoacetic acidHCID 10340Sodium CarbonateHCID 69607379HCID 69607379, Verbindung

Produkt 1

HCID 69607371HCID 69607371, VerbindungAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To PCl15 (854 g, 4.1 mol) in 10 mL anhydrous CH2Cl2 was added cyanoacetic acid (348 g, 4.1 mmol). The reaction mixture was refluxed for 0.5 h, and then 4-(4-Allyloxyphenyl)-2-amino-5-methyl-thiophene-3-carboxylic acid ethyl ester from Example 29B (1.0 g, 3.1 mmol) in 5 ml anhydrous CH2Cl2 was added dropwise at room temperature. The reaction mixture was refluxed for 1 h and cooled to room temperature, and then saturated aq. Na2CO3 was added until pH=7. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo to give the titled compound (1.2 g, 100% yield) as a pale yellow oil which was pure enough to used in next step. 1H NMR (300 MHz, DMSO-d6) δ 11.15 (s, 1H), 7.07 (d, 2H, J=9.0 Hz), 6.97 (d, 2H, J=9.0 Hz), 6.05 (m, 1H), 5.44, 5.38, 5.28, 5.25 (4d, 2H, J=3.0 Hz), 4.60 (d, 2H, J=6.0 Hz), 4.25 (s, 2H), 3.97 (q, 2H, J=6.0 Hz), 2.12 (s, 3H), 0.84 (t, 3H, J=6.0 Hz). MS (ESI) m/e 385 (M+H)+, 383 (M−H)−.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 0.5 h
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5bc21821b112448d90644586373c42fc
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119205B2

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