Phosphorus pentachloride → HCID 12346245, compound

HRID 867953Notes

Reaction equation

HRID 867953 reaction equation
[N+:1]([C:4]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[C:27]([N+:34]([O-:36])=[O:35])[C:5]=1[C:6]([NH:8][NH:9][C:10](=[O:26])[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:12]=1[N+:23]([O-:25])=[O:24])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl>[N+](C1C=CC=CC=1)([O-])=O>[C:5]1([C:6]2[O:26][C:10]([C:11]3[C:12]([N+:23]([O-:25])=[O:24])=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[CH:15][C:16]=3[N+:17]([O-:19])=[O:18])=[N:9][N:8]=2)[C:27]([N+:34]([O-:36])=[O:35])=[CH:28][C:29]([N+:31]([O-:33])=[O:32])=[CH:30][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 12346235HCID 12346235, compound

Product 1

HCID 12346245HCID 12346245, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Dacons, Joseph C.; and Sitzmann, Michael E., Journal of Heterocylic Chemistry, 14, 1151-5 (1977) disclose the cyclization of N,N'-bis(2,4,6-trinitrobenzoyl)hydrazine with PCl5 in nitrobenzene to produce 2,5-dipicryl-1,3,4-oxadiazole in yields of 30-35 percent. Separation of the product 2,5-dipicryl-1,3,4-oxadiazole from nitrobenzene (b.p. 210° C.) is very difficult. The nitrobenzene is removed either by steam distillation or by pouring the nitrobenzene reaction mixture into a second solvent (e.g., methanol) in which 2,5-dipicryl-1,3,4-oxadiazole is much less soluble. However, combining the nitrobenzene with a second solvent makes it quite difficult to recycle the nitrobenzene for further use in the process. In summary, this procedure would be difficult and expensive to scale up for commercial production.

Sources & evidence

ORD record
ord-a8258d0036934da9a95dd4ea3d1141ed
Source dataset
uspto-grants-1988_10
Patent number
US04777258

Reaction notes

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