反応 #349300

反応方程式

4-(β-chloroethylamino)-5-nitro-6-chloropyrimidine

4,6-dichloro-5-nitropyrimidine

β-chloroethylamine hydrochloride

5-nitro-4,6-bis(β-chloroethyl)pyrimidine

sodium bicarbonate

→

7-(β-Chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine

溶媒

chloroform

ether

反応条件

後処理

1. 1
   workup.ADDITIONAn aqueous solution containing 14 g
2. 2
   その他The ether layer was separated
3. 3
   洗浄the separated layer washed with water
4. 4
   その他dried
5. 5
   その他Removal of the ether in vacuo
6. 6
   その他yielded an oil
7. 7
   その他A solid comprising 7-(β-chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride precipitated
8. 8
   その他the precipitate was separated by filtration, 7-(β-chloroethyl)amino-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride
9. 9
   その他thus prepared
10. 10
    その他decomposed at 135° C.
11. 11
    その他after recrystallization from chloroform

実験手順

A solution of 20 g. of 4,6-dichloro-5-nitropyrimidine was prepared in ether. An aqueous solution containing 14 g. of β-chloroethylamine hydrochloride and 24 g. of sodium bicarbonate were added thereto and the subsequent mixture agitated for about 30 minutes. The ether layer was separated, and the separated layer washed with water and dried. Removal of the ether in vacuo yielded an oil containing chiefly 4-(β-chloroethylamino)-5-nitro-6-chloropyrimidine plus a small quantity of 5-nitro-4,6-bis(β-chloroethyl)pyrimidine (the disubstituted product) and a very small quantity of starting material. The oily residue was allowed to stand in chloroform for about one day. A solid comprising 7-(β-chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride precipitated and the precipitate was separated by filtration, 7-(β-chloroethyl)amino-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride thus prepared decomposed at 135° C. after recrystallization from chloroform; yield=5.378 g.

出典