Sulfuric Acid → 2,6-Dichloro-4-(trifluoromethyl)nicotinamide

HRID 2379043Notes

Reaction equation

HRID 2379043 reaction equation
[C:1]([C:3]1[C:4]([Cl:14])=[N:5][C:6]([Cl:13])=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])#[N:2].S(=O)(=O)(O)[OH:16]>>[Cl:14][C:4]1[C:3]([C:1]([NH2:2])=[O:16])=[C:8]([C:9]([F:10])([F:12])[F:11])[CH:7]=[C:6]([Cl:13])[N:5]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 27367262,6-Dichloro-4-(trifluoromethyl)nicotinonitrile

Product 1

HCID 27368742,6-Dichloro-4-(trifluoromethyl)nicotinamide

Procedure

11.3 g of 3-cyano-2,6-dichloro-4-trifluoromethylpyridine was gradually added to 22.6 ml of concentrated sulfuric acid, and then the mixture was heated and reacted at 100° C. for one hour. After completion of the reaction, the mixture was poured into ice water, whereupon white precipitates formed. The precipitates were collected by filtration, and the filtrate was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a white solid. This solid and the precipitates previously obtained, were put together to obtain 9.2 g of 2,6-dichloro-4-trifluoromethyl-3-pyridine carboxamide.

Workup

  1. temperaturethe mixture was heated
  2. customreacted at 100° C. for one hour
  3. customAfter completion of the reaction
  4. customwhereupon white precipitates
  5. customformed
  6. filtrationThe precipitates were collected by filtration
  7. extractionthe filtrate was extracted with methylene chloride
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto obtain a white solid
  11. customThis solid and the precipitates previously
  12. customobtained

Sources & evidence

ORD record
ord-ae4e22098386427b870a5d605f1227d1
Source dataset
uspto-grants-1994_11
Patent number
US05360806

Reaction notes

Loading…