4-Cyanobenzaldehyde → HCID 57762418, Verbindung

HRID 1921127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921127
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[CH3:25][NH:26][C:27](=[O:32])[CH2:28][C:29](=O)[CH3:30]>C1COCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:28]([C:27]([NH:26][CH3:25])=[O:32])=[C:29]([CH3:30])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=3)[C:10](=[S:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

Komponenten

5

Edukt 3

HCID 660424-CyanobenzaldehydeHCID 88483N-MethylacetoacetamideHCID 7358443-(Trifluoromethyl)phenylthiourea

Produkt 1

HCID 57762418HCID 57762418, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Trifluoromethylphenyl thiourea (200 mg, 0.91 mmol), 4-cyanobenzaldehyde (238.2 mg, 1.82 mmol) and N-methyl-3-oxobutanamide (299 mg, 1.82 mmol) are dissolved in 5 ml THF. Ethyl polyphosphate (0.30 g) is added and the reaction mixture is stirred at reflux temperature overnight. After cooling to room temperature, the reaction is quenched with 10 ml of water and extracted with 10 ml ethyl acetate (2×). The combined organic layers are dried with sodium sulfate and the solvent is removed in vacuo. The product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

Aufarbeitung

  1. temperatureat reflux temperature overnight
  2. customthe reaction is quenched with 10 ml of water
  3. extractionextracted with 10 ml ethyl acetate (2×)
  4. dry with materialThe combined organic layers are dried with sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-24752d0b412e4e35b059e2451757e9e8
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173665B2

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