Реакция #6977

ord-55368fddc085434994f442da384179d4

Уравнение реакции

CC[O-].[Na+]
sodium ethoxide
CCOC(=O)c1ccc(N)nc1
ethyl-6-amino-nicotinate
O=C(N=C=S)c1ccccc1
benzoyl isothiocyanate
CCOC(=O)c1ccc(NC(N)=S)nc1
6-thioureido-nicotinic acid ethyl ester
Выход 77.0%

Растворители

Условия реакции

Температура
40°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеthe volatiles were removed in vacuo
  2. 2
    Другоеthe solid formed
  3. 3
    Фильтрацияwas collected by filtration
  4. 4
    Промывкаrinsed with water
  5. 5
    Другоеdried

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07084160B2uspto-grants-2006_08