반응 #76127

반응 방정식

sodium

Chloroacetonitrile

2-amino-4-chloro-5-methylbenzoic acid

→

solid

수율 69.0%

7-Chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one

수율 69.0%

용매

methanol

MeOH

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hours under argon
2. 2
   기타it was fitted with a condenser
3. 3
   기타placed in an oil bath
4. 4
   기타preheated to 80° C
5. 5
   workup.STIRRINGStirring
6. 6
   workup.WAITwas continued at this temperature for 2 hours under argon
7. 7
   온도to cool to room temperature
8. 8
   여과The precipitate was collected by filtration
9. 9
   세척washed with methanol (10 ml), and water (10 ml)
10. 10
    건조dried in vacuo over P2O5

실험 절차

To a flask containing sodium (36 mg) was added anhydrous MeOH (5 ml). Chloroacetonitrile (0.520 g, 6.9 mmol) was then added and the clear solution was stirred at room temperature for 30 min under argon. A solution of 2-amino-4-chloro-5-methylbenzoic acid (1.13 g, 6.0 mmol) in anhydrous methanol (25 ml) was then added with a syringe via a rubber septum. The reaction mixture was stirred at room temperature for 2 hours under argon, then it was fitted with a condenser and placed in an oil bath preheated to 80° C. Stirring was continued at this temperature for 2 hours under argon, then the reaction mixture was allowed to cool to room temperature. The precipitate was collected by filtration, washed with methanol (10 ml), and water (10 ml), and dried in vacuo over P2O5 to afford a grey solid (1.0 g, 69%), mp 287-290° C.; 1H-NMR (DMSO-d6) 2.47 (s, 3H, 6-CH3), 4.53 (s, 2H, CH2Cl), 7.75, 8.08 (2×s, 2H, 5-H and 8-H); 12.60 (s, 1H, N3—H); MS (FAB, m/z) 243, 244, 245 (M+H)+.

출처