反応 #5911

反応方程式

sodium hydride

phosphoric acid

6-imidazolylsalicylic acid

1-chloro-3,5-dimethoxy-s-triazine

N-hydroxypyrazole

→

6-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred for a further 14 hours
2. 2
   抽出hydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether
3. 3
   乾燥The organic phases are dried over sodium sulfate
4. 4
   その他evaporated down under reduced pressure
5. 5
   workup.STIRRINGAfter the mixture has been stirred for 30 minutes at room temperature
6. 6
   workup.STIRRINGthe whole is stirred for 14 hours
7. 7
   抽出extracted with diethyl ether
8. 8
   乾燥The ether phase is dried over sodium sulfate
9. 9
   その他evaporated down
10. 10
    その他the residue is purified by column chromatography

実験手順

1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of 1.88 g (10 mmol) of 6-imidazolylsalicylic acid in 30 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 9.9 mmol of N-hydroxypyrazole is added and the mixture is stirred for a further 14 hours. The reaction mixture is then hydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether. The organic phases are dried over sodium sulfate and evaporated down under reduced pressure. The residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium hydride (85% strength in paraffin, 10 mmol) is added. After the mixture has been stirred for 30 minutes at room temperature, 1.58 g (9 mmol) of 1-chloro-3,5-dimethoxy-s-triazine is added and the whole is stirred for 14 hours. The batch is introduced into 300 ml of 0.1N phosphoric acid, and extracted with diethyl ether. The ether phase is dried over sodium sulfate and evaporated down, and the residue is purified by column chromatography.

出典