Oxalyl chloride → HCID 10376503, compound

HRID 325124Notes

Reaction equation

HRID 325124 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 chromatogrphed on silica gel using hexane/CH2Cl2 (1:1) to give 2-chloro-1,4-dinitrocubane 3, m.p. 145-147° C.; 1H NMR (CDCl3); δ 4.84 (m, 2H); 4.71 (m, 3H); and 2,5-dichloro-1,4-dinitrocubane, 4, m.p. 188-190° C.; 1H NMR (CDCl3); δ 4.90 (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

Sources & evidence

ORD record
ord-c6db209e269644aabca8e2b11a9429c3
Source dataset
uspto-grants-2001_04
Patent number
US06222068B1

Reaction notes

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