Dichloromethane → HCID 12878834, compound

HRID 1762713Notes

Reaction equation

HRID 1762713 reaction equation
Cl.[Cl:2][C:3]([Cl:11])([Cl:10])[C:4]1[CH:5]=[NH+:6][CH:7]=[CH:8][CH:9]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:2][C:3]([Cl:11])([Cl:10])[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 20041740HCID 20041740, compound

Product 1

HCID 12878834HCID 12878834, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The 3-trichloromethylpyridinium hydrochloride salt (2836 g, 12.17 moles) was placed in a 22-liter pot with 2800 ml of methylene chloride and 2600 ml of water. A solution of 1000 g of sodium carbonate in 4300 ml of water was then added slowly so that the gassing could be controlled. The temperature was maintained with an ice bath between 15°-20° C. The lower organic phase was then separated and was dried with magnesium sulfate. The mixture was filtered and the methylene chloride was removed by rotary evaporation. The concentrated material was distilled at 77°-79° C. and 0.5 mm Hg giving 1918 g of the desired 3-trichloromethylpyridine product. The yield was 80%.

Workup

  1. temperatureThe temperature was maintained with an ice bath between 15°-20° C
  2. customThe lower organic phase was then separated
  3. dry with materialwas dried with magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe methylene chloride was removed by rotary evaporation
  6. distillationThe concentrated material was distilled at 77°-79° C.

Sources & evidence

ORD record
ord-6f7d1684ad824d5abf338448017d129b
Source dataset
uspto-grants-1989_05
Patent number
US04833250

Reaction notes

Loading…