반응 #78616

반응 방정식

4-aminobenzonitrile

2-methoxymethylthiazolo[5,4-b]pyridin-6-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

boron tribromide

→

crude product

2-[N-(4-Cyanophenyl)aminomethyl]thiazolo[5,4-b]pyridin-6-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   세척Then the mixture was washed with 40 mL of saturated sodium hydrogen carbonate solution
2. 2
   건조the organic phase was dried with sodium sulfate
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   온도heated
5. 5
   workup.WAITto boiling for one hour
6. 6
   workup.DISTILLATIONThen the solvent was distilled off in vacuo
7. 7
   세척the organic phase was washed with 100 mL of water
8. 8
   건조dried with sodium sulfate
9. 9
   기타After the solvent had been removed in vacuo

실험 절차

A mixture of 1.54 g (3.85 mmol) of 2-methoxymethylthiazolo[5,4-b]pyridin-6-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide and 4.3 mL (4.3 mmol) of a 1 molar solution of boron tribromide in methylene chloride was dissolved in a further 30 mL of methylene chloride and stirred for 5 hours at room temperature. Then the mixture was washed with 40 mL of saturated sodium hydrogen carbonate solution, the organic phase was dried with sodium sulfate, and the solvent was distilled off. The crude product (1.9 g) was taken up in 15.0 mL of N,N-diisopropylethylamine, mixed with 0.50 g (4.2 mmol) of 4-aminobenzonitrile, and heated to boiling for one hour. Then the solvent was distilled off in vacuo, the crude product was taken up in 100 mL of methylene chloride, the organic phase was washed with 100 mL of water, and dried with sodium sulfate. After the solvent had been removed in vacuo, the crude product obtained was purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=35:65 to 1:1) and evaporated down again in vacuo. Yield: 0.45 g (24% of theory) of yellow amorphous solid; Rf value: 0.34 (silica gel; ethyl acetate/petroleum ether=1:1).

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