反応 #76127

反応方程式

sodium

Chloroacetonitrile

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

→

solid

収率 69.0%

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

収率 69.0%

溶媒

methanol

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 hours under argon
2. 2
   その他it was fitted with a condenser
3. 3
   その他placed in an oil bath
4. 4
   その他preheated to 80° C
5. 5
   workup.STIRRINGStirring
6. 6
   workup.WAITwas continued at this temperature for 2 hours under argon
7. 7
   温度to cool to room temperature
8. 8
   ろ過The precipitate was collected by filtration
9. 9
   洗浄washed with methanol (10 ml), and water (10 ml)
10. 10
    乾燥dried in vacuo over P2O5

実験手順

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)+.

出典