Hydrochloric Acid → HCID 17271754, compound

HRID 2246063Notes

Reaction equation

HRID 2246063 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].C1COCC1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].Cl>O.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:16]([CH3:15])(=[O:18])=[O:17])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chloride2×HCID 965953,5-Difluoroaniline

Product 1

HCID 17271754HCID 17271754, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The reactor is charged with 14.0 kg of 3,5-difluoroaniline and 56 liters of THF. 9.6 kg of pyridine are added to the stirred solution. The reaction medium is cooled to 0° C. and 13.10 kg of methanesulfonyl chloride are added, while maintaining the temperature between 0-10° C. for 1 hour 30 minutes. At the end of introduction of the methanesulfonyl chloride, the reaction medium is heated at 25° C. for 2 hours. 29 liters of demineralized water and then 6.6 kg of hydrochloric acid (30% w/w) are added to the reaction medium. 60 liters of solvent are distilled off at atmospheric pressure in the presence of an external bath maintained at 100° C., and the reaction medium is then cooled to 20° C. The resulting suspension is filtered and the solid is washed with a total of 20 liters of demineralized water. The solid is dried under vacuum (20 m bar) at 40° C. until a water content <0.5% is obtained. 19.48 kg (87%) of a slightly yellow crystalline solid are thus obtained (m.p.: 121° C.).

Workup

  1. temperaturewhile maintaining the temperature between 0-10° C. for 1 hour 30 minutes
  2. distillation60 liters of solvent are distilled off at atmospheric pressure in the presence of an external bath
  3. temperaturemaintained at 100° C.
  4. temperaturethe reaction medium is then cooled to 20° C
  5. filtrationThe resulting suspension is filtered
  6. washthe solid is washed with a total of 20 liters of demineralized water
  7. dry with materialThe solid is dried under vacuum (20 m bar) at 40° C. until a water content <0.5%
  8. customis obtained
  9. custom19.48 kg (87%) of a slightly yellow crystalline solid are thus obtained (m.p.: 121° C.)

Sources & evidence

ORD record
ord-edf6a6099e1b454b82a341ed7d6f81b0
Source dataset
uspto-grants-2010_03
Patent number
US07687493B2

Reaction notes

Loading…