Oxalyl chloride → HCID 10376503, compound

HRID 2255806Notes

Reaction equation

HRID 2255806 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(Cl)(=O)C([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]

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 11745511HCID 11745511, compound

Product 1

HCID 10376503HCID 10376503, compound

Procedure

A mixture of 1,4-dinitrocubane, 1, (388 mg, 2.0 mmol) in oxalyl chloride (50 mL) was photolyzed under a sunlamp for 18 h at room temperature. Oxalyl chloride was removed on a rotary evaporator and the solid residue was partioned between EtOAc (40 mL) and NaOH solution (5%, 30 mL). After stirring for 3 h, the organic phase was separated, washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel using hexane/CH2Cl2 (1:1) to give 2-chloro-1,4-dinitrocubane 3, m.p. 145°-147° C.; 1H NMR (CDCl3); δ4.84 (m, 2H); 4.71 (m, 3H); and 2,5-dichloro-1,4-dinitrocubane, 4, m.p. 188°-190° C.; 1H NMR (CDCl3); δ4.90 (dd, 2H); 4.78 (dd, 2H).

Workup

  1. customOxalyl chloride was removed on a rotary evaporator
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-36078f931b8d41c5b484d29c0ed945ff
Source dataset
uspto-grants-1993_08
Patent number
US05241116

Reaction notes

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