Benzoyl isothiocyanate → 6-Thioureido-nicotinic acid ethyl ester

HRID 1985766

Reaktionsgleichung

Reaktionsgleichung von HRID 1985766
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][CH:6]=1)[CH3:2].C([N:21]=[C:22]=[S:23])(=O)C1C=CC=CC=1.[O-]CC.[Na+]>C1COCC1.C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:22]([NH2:21])=[S:23])=[N:7][CH:6]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 68284Benzoyl isothiocyanateHCID 235927Ethyl 6-AminonicotinateHCID 2723922Sodium ethoxide

Produkt 1

HCID 220190876-Thioureido-nicotinic acid ethyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of ethyl-6-amino-nicotinate (2.5 g, 15 mmol) and benzoyl isothiocyanate (2.45 g, 15 mmol) in THF (20 mL) was heated at 40° C. for 4 h. To this mixture at RT, was added sodium ethoxide (2.04 g, 30 mmol) in ethanol (10 mL). After stirring the resulting mixture at RT for 16 h, the volatiles were removed in vacuo. The residue was suspended in aqueous NH4Cl and the solid formed was collected by filtration, rinsed with water and dried to afford 6-thioureido-nicotinic acid ethyl ester as a white solid (2.6 g, 77% yield). LC/MS; (M+H)+=226.

Aufarbeitung

  1. customthe volatiles were removed in vacuo
  2. customthe solid formed
  3. filtrationwas collected by filtration
  4. washrinsed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-93eb81c6b7a541f8ac484d890aa60477
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547711B2

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