Oxalyl chloride → HCID 10376503, compound

HRID 325123Notes

Reaction equation

HRID 325123 reaction equation
[N+:1]([C:4]12[CH:11]3[CH:6]4[C:7]5([N+:12]([O-:14])=[O:13])[CH:10]3[CH:9]1[CH:8]5[CH:5]24)([O-:3])=[O:2].[C:15]([Cl:20])(=O)[C:16]([Cl:18])=O>>[Cl:18][C:8]12[CH:5]3[CH:6]4[CH:11]5[C:4]3([N+:1]([O-:3])=[O:2])[CH:9]1[CH:10]5[C:7]24[N+:12]([O-:14])=[O:13].[Cl:18][C:16]12[CH:11]3[CH:6]4[CH:5]5[C:4]3([N+:1]([O-:3])=[O:2])[C:15]1([Cl:20])[CH:8]5[C:7]24[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 11745511HCID 11745511, compound

Product 2

HCID 10376503HCID 10376503, compoundHCID 11097378HCID 11097378, compound

Procedure

A solution of 1,4-dinitrocubane (Eaton, P. E.; et al; J. Org. Chem.; 1984, 49, 185; Eaton, P. E.; Wicks, G. E.; J. Org. Chem.; 1988, 53, 5353) in oxalyl chloride was irradiated under a sunlamp for 12 h at room temperature. After removing oxalyl chloride under reduced pressure, the reaction mixture was hydrolyzed and partioned between ethyl acetate and 5% aqueous NaOH. From the organic phase was isolated 2-chloro-1,4-dinitrocubane, 3, and 2,5-dichloro-1,4-dinitrocubane, 4. After acidification of the alkaline layer with HCl and extraction with ethyl acetate, 2-carboxy-1,4-dinitrocubane, 5, was obtained in 68% yield.

Workup

  1. customAfter removing oxalyl chloride under reduced pressure

Sources & evidence

ORD record
ord-327e5b6b73b8436bb92359b5de9ccb06
Source dataset
uspto-grants-2001_04
Patent number
US06222068B1

Reaction notes

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