Oxalyl chloride → HCID 10376503, compound

HRID 249566Notes

Reaction equation

HRID 249566 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-63aa748574b5458c839044273acbbe05
Source dataset
uspto-grants-1993_05
Patent number
US05214222

Reaction notes

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