تفاعل #1769055

ord-a713f6be2aa04ac2bddbc2d06f5e6cef

معادلة التفاعل

OCc1ccccc1
benzyl alcohol
Cl.O=C(O)C1CN=CNC1
1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride
O=S(Cl)Cl
thionyl chloride
CCOCC
ethyl ether
Cl.O=C(OCc1ccccc1)C1CN=CNC1
product
المردود 76.0%
Cl.O=C(OCc1ccccc1)C1CN=CNC1
Benzyl 1,4,5,6-Tetrahydropyrimidine-5-carboxylate Hydrochloride
المردود 76.0%

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىprecipitation
  2. 2
    أخرىThe white solids were collected
  3. 3
    أخرىcrystallized from methanol/THF

الإجراء التجريبي

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.0 g, 6.1 mmol) was suspended in dry benzyl alcohol (20 ml). To the mixture was added thionyl chloride (0.76 g, 6.39 mmol) and the resulting mixture was heated in an oil bath at 80° C. for 24 h. The clear solution was poured to anhydrous ethyl ether (100 ml) to induce precipitation. The white solids were collected and crystallized from methanol/THF to give 1.18 g (76%) of product (mp 113°-114° C.). 300 MHz nmr indicated the product. Microanalysis calc.: C 56.58, H 5.89, N 11.00; found: C 56.34, H 6.03, N 11.19.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05175166uspto-grants-1992_12