Реакция #350987

Уравнение реакции

ethanolamine

N-(2 -hydroxyethyl)-3-[4-(3,3,3-triphenylpropoxy)phenyl]propionamide

hydrochloride monohydrate

thionyl chloride

→

title compound

Выход 85.0%

4,5-Dihydro-2-{2-[4-(3,3,3-triphenylpropoxy)phenyl]ethyl}oxazole

Выход 85.0%

Растворители

EtOAc

EtOAc

Условия реакции

Обработка

1. 1
   Другоеthe precipitate was collected
2. 2
   Промывкаwashed with EtOAc

Методика

By the method of example 25, ethanolamine was converted to N-(2 -hydroxyethyl)-3-[4-(3,3,3-triphenylpropoxy)phenyl]propionamide. To this amide (400 mg; 0.84 mmol) in EtOAc (15 mL), was added dropwise over 5 minutes thionyl chloride (0.20 mL, 2.74 mmol) in EtOAc (2 mL) under a nitrogen atmosphere at room temperature. After stirring overnight, the precipitate was collected and washed with EtOAc to give the title compound (354.1 mg; 85% yield) as the hydrochloride monohydrate, a white powder. mp=130°-131° C. 1H NMR δ 7.19-7.34 (m, 15H), 7.02 (d, J=8.6 Hz, 2H), 6.62 (d, J=8.6 Hz, 2H), 3.70 (t, J=7.7 Hz, 2H), 3.53 (br s, 4H), 3.12 (t, J=7.7 Hz, 2H), 2.87 (t, J=7.5 Hz, 2H), 2.43 (t, J=7.5 Hz, 2H). IR 2954, 1513, 1245 cm-1. MS 462 (MH+), 243. Anal. calcd. for C32H31NO2.HCl.H2O: C, 74.48; H, 6.48; N, 2.71. Found: C, 74.26; H, 6.32; N, 2.70.

Источник