Potassium Carbonate → (4-Pyridin-4-yl-phenyl)-thiourea

HRID 2076134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076134
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C([N:22]=[C:23]=[S:24])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:23]([NH2:22])=[S:24])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 15126544-(Pyridin-4-yl)aniline

Produkt 1

HCID 86632614(4-Pyridin-4-yl-phenyl)-thioureaAusbeute 152,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-pyridin-4-yl-phenylamine (142 mg, 0.83 mmol) in tetrahydrofurane (5 mL) was added drop wise under benzoyl isothiocyanate (124 uL, 0.88 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and a solution of potassium carbonate (346 mg, 2.5 mmol) in water (3 mL) was added. The resulting suspension was stirred at room temperature over night. The precipitate was filtered off, washed with water and diethyl ether to yield the title compound as a pale yellow solid (291 mg, 152%). MS ISP (m/e): 230.2 (56) [(M+H)+], 213.0 (100) [(M-NH3+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.86 (s, 1H, NH), 8.61 (d, 2H), 7.79 (d, 2H), 7.69 (d, 1H), 7.61 (d, 2H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (6 mL)
  3. stirringThe resulting suspension was stirred at room temperature over night
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-36fb475ce95b4f3ebacbd30f437b9e8d
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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