Acetic Acid → 1-thioureido-1H-pyrrole-2-carboxamide

HRID 1685966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685966
C([NH:9][C:10](=[S:20])[NH:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO.C(O)(=O)C>O.CC(C)=O>[NH:11]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])[C:10]([NH2:9])=[S:20]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 100626351-(((Benzoylamino)thioxomethyl)amino)-1H-pyrrole-2-carboxamide

Produkt 1

HCID 104650001-thioureido-1H-pyrrole-2-carboxamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Compound 1A (2.2 g, 7.6 mmol) was treated with a solution of K2CO3 (2.0 g, 14.8 mmol) in water (9 mL) at ambient temperature. Methyl alcohol (70 mL) and acetone (70 mL) were added and the mixture was heated to reflux for 18 hours. The reaction was cooled to ambient temperature and treated with acetic acid (2.0 mL, 35 mmol), and then concentrated to approximately 30 mL. The resulting suspension was cooled to 0° C. and the product was recovered by vacuum filtration to afford 1B (1.1 g, 79%). HPLC tR=0.405 min (YMC S5 Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). 1H NMR (400 MHz, DMSO-d6) δ 10.4 (s, 1H), 8.13 (br s, 2H), 7.31 (br s, 1H), 7.10 (br s, 1H), 6.88 (t, 1H, J=2.0 Hz), 6.75 (dd, 1H, J=1.6, 4.0 Hz), 6.05 (t, 1H, J=3.6 Hz).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated to approximately 30 mL
  4. temperatureThe resulting suspension was cooled to 0° C.
  5. filtrationthe product was recovered by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-547bede71ccb4eb18ee166d62bdbd407
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148523B2

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