반응 #1106608

반응 방정식

N,N-diethylaniline hydrochloride

1,2-bis(trifluoroacetyl)hydrazine

phosphoryl chloride

→

2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene

수율 53.0%

반응 조건

후처리

1. 1
   기타fitted with a condenser
2. 2
   기타leading to a cold trap
3. 3
   기타(−78° C.)
4. 4
   온도The mixture was heated
5. 5
   온도under reflux for 5 h
6. 6
   온도to cool
7. 7
   workup.WAITstored overnight
8. 8
   기타condensed in the cold trap
9. 9
   기타the two layers which had formed
10. 10
    기타were separated
11. 11
    workup.ADDITIONThe layer was added to ice water (85 mL)
12. 12
    workup.STIRRINGthe mixture vigorously stirred for 1 h in a flask
13. 13
    기타fitted with a condenser
14. 14
    기타Separation of the lower organic layer
15. 15
    기타gave the main batch of the crude product (6.4 g)
16. 16
    기타the organic layer subjected to preliminary purification by trap-to-trap
17. 17
    workup.DISTILLATIONdistillation in vacuum
18. 18
    기타to afford a second batch of crude product (1.6 g)
19. 19
    workup.DISTILLATIONDistillation of the combined product through a vacuum-jacketed Vigreux column

실험 절차

A mixture of N,N-diethylaniline hydrochloride (18.5 g, 0.1 mol), 1,2-bis(trifluoroacetyl)hydrazine (10.3 g, 0.46 mol) and phosphoryl chloride (160 mL) was stirred for 30 minutes under nitrogen in a flask fitted with a condenser leading to a cold trap (−78° C.). The mixture was heated under reflux for 5 h and then allowed to cool and stored overnight. The flask contents and the small amount of material which had condensed in the cold trap were combined and the two layers which had formed were separated. The layer was added to ice water (85 mL) and the mixture vigorously stirred for 1 h in a flask fitted with a condenser. Separation of the lower organic layer gave the main batch of the crude product (6.4 g). The original dark upper layer was treated similarly with ice water (75 mL) and the organic layer subjected to preliminary purification by trap-to-trap distillation in vacuum to afford a second batch of crude product (1.6 g). Distillation of the combined product through a vacuum-jacketed Vigreux column gave 2,5-dichloro-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene (6.3 g, 53%) as an oil.

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