Реакция #1135792

Уравнение реакции

sodium nitrite

hydrochloric acid

aluminum chloride

sodium azide

1-fluoro-3-isocyanato-2-methylbenzene

→

1-(2-methyl-3-fluorophenyl)-1,4-dihydrotetrazole-5-one

Выход 95.1%

Растворители

water

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting mixtures were stirred for fifteen minutes
2. 2
   ТемператураAfter cooling the mixtures
3. 3
   workup.ADDITIONwas added the reaction solutions
4. 4
   workup.STIRRINGwith stirring
5. 5
   Экстракцияwere extracted with ethyl acetate
6. 6
   ПромывкаThe organic layers were washed with water and saturated saline
7. 7
   Сушкаwere dried over anhydrous magnesium sulfate
8. 8
   Концентрированиеwere then concentrated under reduced pressure

Методика

Under ice-cooling, to N,N-dimethylformamide 250 mL was added anhydrous aluminum chloride 21.9 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 10.7 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-fluoro-3-isocyanato-2-methylbenzene 22.5 g and the resulting mixtures were heated at 80° C. for three and a half hours. After cooling the mixtures, to a mixture of sodium nitrite 34 g, water 2 L and ice 500 g was added the reaction solutions with stirring. The mixtures were acidified with 10% hydrochloric acid and were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-fluorophenyl)-1,4-dihydrotetrazole-5-one 27.5 g.

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