Chlorine → 2,3-Dichloro-5-(trichloromethyl)pyridine

HRID 2164888Notes

Reaction equation

HRID 2164888 reaction equation
[Cl:1]C(C1C=CC=CN=1)(Cl)Cl.[Cl:11][C:12]1[N:17]=[CH:16][C:15]([C:18]([Cl:21])([Cl:20])[Cl:19])=[CH:14][C:13]=1C(Cl)(Cl)Cl.ClCl>>[Cl:1][C:13]1[CH:14]=[C:15]([C:18]([Cl:21])([Cl:20])[Cl:19])[CH:16]=[N:17][C:12]=1[Cl:11]

Participants

4

Reactant 3

HCID 24526ChlorineHCID 123215Pyridine, 2-(trichloromethyl)-HCID 133826392-Chloro-3,5-bis(trichloromethyl)pyridine

Product 1

HCID 946472,3-Dichloro-5-(trichloromethyl)pyridine

Procedure

Seventy-five grams of a mixture containing 24.3% 3,5-bis(trichloromethyl pyridine and 6.5% 6-chloro-3,5-bis(trichloromethyl)pyridine were chlorinated with 70 grams per hour of chlorine at 190° C. for 8 hours. Analysis is listed in Table 8. The 5,6-dichloro-3-trichloromethyl pyridine concentration went from zero to 0.5% and the 2,6-dichloro-3,5-bis(trichloromethyl)pyridine went from zero to 0.7%. The 3,5-bis(trichloromethyl)pyridine went from 24.3% to 18.1% while the 6-chloro-3,5-bis(trichloromethyl)pyridine increased from 6.5% to 14.0%. Temperatures below 190° C. give unacceptably slow reaction rates to produce 5,6-dichloro-3-trichloromethyl pyridine and 2,3,5,6-tetrachloropyriidine.

Workup

  1. concentrationThe 5,6-dichloro-3-trichloromethyl pyridine concentration
  2. temperatureincreased from 6.5% to 14.0%
  3. customTemperatures below 190° C. give unacceptably slow
  4. customreaction rates

Sources & evidence

ORD record
ord-269c154340ca4ee1ab50e34d9431bef0
Source dataset
uspto-grants-1985_03
Patent number
US04507486

Reaction notes

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