Thionyl Chloride → HCID 21568139, compound

HRID 1579218Notes

Reaction equation

HRID 1579218 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH:7]([C:17](O)=[O:18])[O:8][C:9]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[NH2:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>C1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[CH:15][C:9]2[O:8][CH:7]([C:17]([NH:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:18])[O:6][C:5]3[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][C:4]=3[CH2:11][C:10]=2[CH:12]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 310183-PyridinemethanamineHCID 21568136HCID 21568136, compound

Product 1

HCID 21568139HCID 21568139, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 15 g of 2,10-dichloro-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic acid was added 75 ml of thionyl chloride, and the heterogenous mixture was refluxed with occasional stirring until it became homogenous. The mixture was refluxed for an additional 2 hours after which the thionyl chloride was distilled off under reduced pressure affording a solid residue which was dissolved in 300 ml of dry benzene by warming on a steam bath. The benzene was distilled off under reduced pressure affording a white crystalline residue to which was added 500 ml of dry benzene. The mixture was stirred at room temperature until homogenous then 35 g of 3-aminomethylpyridine was added. After standing at room temperature for 2 hours the mixture was heated to reflux for an additional 3 hours, cooled to room temperature, poured into ice water and separated. Methanol was added to aid the solubility of the product in the organic layer. The organic layer was washed with water and distilled under reduced pressure resulting in a residue which was dried and recrystallized twice from methanol-acetone (1:1) to give the desired product, M.P. 225°-226°C.

Workup

  1. temperaturethe heterogenous mixture was refluxed
  2. distillationwas distilled off under reduced pressure
  3. customaffording a solid residue which
  4. temperatureby warming on a steam bath
  5. distillationThe benzene was distilled off under reduced pressure
  6. customaffording a white crystalline residue to which
  7. additionwas added
  8. temperaturethe mixture was heated
  9. temperatureto reflux for an additional 3 hours
  10. customseparated
  11. additionMethanol was added
  12. washThe organic layer was washed with water
  13. distillationdistilled under reduced pressure
  14. customresulting in a residue which
  15. customwas dried
  16. customrecrystallized twice from methanol-acetone (1:1)

Sources & evidence

ORD record
ord-663c4236920d4229b376220658b75e77
Source dataset
uspto-grants-1976_01
Patent number
US03931173

Reaction notes

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