반응 #11447

반응 방정식

tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate

Phenol

sodium hydride

→

tert-butyl 4-[(6-methyl-3-nitro-2-phenoxypyridin-4-yl)amino]butylcarbamate

수율 64.5%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도a chilled
2. 2
   온도while maintaining the reaction mixture at 0° C
3. 3
   온도to warm to ambient temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   농축before being concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (500 mL)
7. 7
   세척washed with 1N sodium hydroxide (300 mL)
8. 8
   건조dried over magnesium sulfate
9. 9
   농축concentrated to dryness
10. 10
    기타The crude product was purified by column chromatography (400 g silica gel eluting with 7:3 hexanes

실험 절차

Phenol (9.45 g, 100 mmol) was added over a period of 10 minutes to a chilled (0° C.) suspension of sodium hydride (4.24 g of 60%, 106 mmol) in anhydrous tetrahydrofuran (100 mL). The reaction mixture was allowed to stir at 0° C. for 30 minutes. A solution of tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate (33.92 g, 94.5 mmol) in anhydrous tetrahydrofuran (250 mL) was added over a period of 50 minutes while maintaining the reaction mixture at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred overnight before being concentrated under reduced pressure. The residue was dissolved in ethyl acetate (500 mL), washed with 1N sodium hydroxide (300 mL), dried over magnesium sulfate and then concentrated to dryness. The crude product was purified by column chromatography (400 g silica gel eluting with 7:3 hexanes:ethyl acetate to provide 25.4 g of tert-butyl 4-[(6-methyl-3-nitro-2-phenoxypyridin-4-yl)amino]butylcarbamate.

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