Реакция #214665

Уравнение реакции

dichloroacetyl chloride

cyclohexanone

2-mercaptoethylamine

benzene

→

product

N-dichloroacetyl-1-thia-4-azaspiro[4,5]decane

Растворители

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONFrom a boiling mixture of 9.8 g
2. 2
   workup.DISTILLATIONis continuously distilled off
3. 3
   Другоеof water are separated
4. 4
   ТемператураThe reaction mixture is then cooled
5. 5
   workup.ADDITIONof a 40% aqueous sodium hydroxide solution are added
6. 6
   workup.ADDITIONfollowed by dropwise addition of 14.7 g
7. 7
   Промывкаwashed with aqueous hydrochloric acid solution and subsequently with water
8. 8
   ДругоеFrom the neutral mixture obtained benzene
9. 9
   workup.DISTILLATIONis distilled off in vacuo
10. 10
    Другоеto give 17.2 g
11. 11
    ДругоеRecrystallization from absolute ethanol

Методика

From a boiling mixture of 9.8 g. (0.1 moles) of cyclohexanone and 7.7 g. (0.1 moles) of 2-mercaptoethylamine in 100 ml. of benzene the water formed is continuously distilled off. Boiling is continued until 1.8 ml. of water are separated. The reaction mixture is then cooled and 11 g. of a 40% aqueous sodium hydroxide solution are added followed by dropwise addition of 14.7 g. (0.1 moles) of dichloroacetyl chloride, with external salt/ice cooling. Mixture is stirred for a further two hours at room temperature and washed with aqueous hydrochloric acid solution and subsequently with water. From the neutral mixture obtained benzene is distilled off in vacuo to give 17.2 g. (0.064 moles) of a white powder. Recrystallization from absolute ethanol yields a white crystalline product melting at 149° to 151° C. The structure of the named compound can be verified by IR spectrum analysis.

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