반응 #4535

반응 방정식

acetic acid

potassium acetate

3-chloromethyl-5-dichloromethyl-2-phthalimidopyrazine

dichloromethane

→

3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine

수율 77.0%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   workup.ADDITIONthe resulting mixture was mixed thoroughly
2. 2
   기타phase separation
3. 3
   추출The aqueous phase was extracted once with 500 ml of dichloromethane and once with 250 ml of dichloromethane
4. 4
   세척The combined organic phases were washed twice with 1,000 ml of water
5. 5
   건조dried over sodium sulfate
6. 6
   기타evaporated down in a rotary evaporator
7. 7
   workup.WAITthe solution was left
8. 8
   기타to crystallize at room temperature
9. 9
   여과filtered off
10. 10
    기타dried
11. 11
    기타The crystals were then recrystallized again from methanol

실험 절차

50 ml of absolute glacial acetic acid and 35 g of potassium acetate were added to a solution of 57.7 g (0.16 mole) of 65% strength 3-chloromethyl-5-dichloromethyl-2-phthalimidopyrazine in 1,000 ml of dimethyl sulfoxide, and the mixture was then stirred for three days at room temperature. Thereafter, 1,000 ml of dichloromethane and 1,000 ml of ice-water were added to the reaction mixture, the resulting mixture was mixed thoroughly, and phase separation was effected. The aqueous phase was extracted once with 500 ml of dichloromethane and once with 250 ml of dichloromethane. The combined organic phases were washed twice with 1,000 ml of water, dried over sodium sulfate and evaporated down in a rotary evaporator. The blackish brown oil was taken up in 20 ml of methanol at the boil, and the solution was left to crystallize at room temperature. The product was then suspended in a little diethyl ether, filtered off and dried. The crystals were then recrystallized again from methanol. 30.6 g (77% of theory) of 3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine of melting point 117°-118° C. were obtained. 1H-NMR (270 MHz, CDCl3): δ1.9 (s, 3H), 5.3 (s, 2H), 6.9 (s, 1H), 8.1 (m, 4H), 9.1 (s, 1H).

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