Thionyl Chloride → 5-(Chloro)carbonyl-6-nitro-1,3-benzodioxole

HRID 1729203Notes

Reaction equation

HRID 1729203 reaction equation
[CH2:1]1[O:12][C:11]2[C:3](=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=2)[C:7](O)=[O:8])[O:2]1.S(Cl)([Cl:18])=O>>[CH2:1]1[O:12][C:11]2[C:3](=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=2)[C:7]([Cl:18])=[O:8])[O:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acid

Product 1

HCID 155638945-(Chloro)carbonyl-6-nitro-1,3-benzodioxole

Procedure

5 g (0.23 mole) of 4,5-methylenedioxy-2-nitrobenzoic acid are suspended in 50 ml of thionyl chloride and refluxed for 2 hours. The solution obtained is concentrated under reduced pressure. The residual oil crystallizes immediately after the addition of 50 ml of petroleum ether. The crystals are spun and recrystallized in ether.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solution obtained
  3. concentrationis concentrated under reduced pressure
  4. customThe residual oil crystallizes immediately
  5. additionafter the addition of 50 ml of petroleum ether
  6. customrecrystallized in ether

Sources & evidence

ORD record
ord-060e3bda1d9443359733d5c7239da5fd
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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