反応 #75991

反応方程式

tert-butyl isothiocyanate

triethylamine

(2R)-2-amino-3-(3-thienyl)-1-propanol hydrochloride

→

N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-thienylmethyl)ethyl]thiourea

溶媒

ethanol

water

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 66 hours at room temperature
2. 2
   その他the reaction medium is evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C
3. 3
   その他The thick brown oil obtained
4. 4
   抽出extracted with twice 12 cm3 of ethyl acetate
5. 5
   ろ過The organic phase is filtered through Celite
6. 6
   洗浄washed with twice 4 cm3 of saturated aqueous sodium chloride solution
7. 7
   乾燥dried over magnesium sulfate
8. 8
   その他evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C
9. 9
   その他A brown oil is obtained
10. 10
    その他which crystallizes rapidly under cold conditions and which
11. 11
    その他is dried in an oven under vacuum (10 Pa) at a temperature in the region of 48° C.

実験手順

0.9 cm3 of tert-butyl isothiocyanate and then 0.82 cm3 of triethylamine are added to a suspension of 0.9 g of (2R)-2-amino-3-(3-thienyl)-1-propanol hydrochloride in 9 cm3 of absolute ethanol stirred and under an inert atmosphere. After stirring for 66 hours at room temperature, the reaction medium is evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. The thick brown oil obtained is taken up in 6 cm3 of water and then extracted with twice 12 cm3 of ethyl acetate. The organic phase is filtered through Celite and washed with twice 4 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. A brown oil is obtained, which crystallizes rapidly under cold conditions and which is dried in an oven under vacuum (10 Pa) at a temperature in the region of 48° C. to give 0.97 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-thienylmethyl)ethyl]thiourea in the form of a beige-colored solid melting at 109° C. 1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 1.43 (s: 9H); 2.84 (mt: 2H); 3.38 (mt: 2H); 4.42 (unres. mult.: 1H); 4.86 (broad t, J=4.5 Hz: 1H); 7.04 (broad d, J=5 Hz: 1H); from 7.10 to 7.20 (mt: 2H); 7.25 (broad s: 1H); 7.46 (dd, J=5 and 3 Hz: 1H).

出典