Pyridine → 2-Chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate

HRID 18676Notes

Reaction equation

HRID 18676 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:8][C:7]=1[S:26]([NH-:29])(=[O:28])=[O:27].N1C=CC=CC=1.[C:36](Cl)(Cl)=[O:37]>ClCCCl>[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:8][C:7]=1[S:26]([N:29]=[C:36]=[O:37])(=[O:27])=[O:28]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 24386Thionyl ChlorideHCID 866077562-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylamide

Product 1

HCID 587094392-Chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

At 60° C., 7.4 g (62.3 mmol) of thionyl chloride were added dropwise with stirring to a suspension of 10.0 g (24.9 mmol) of 2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylamide in 1,2-dichloroethane. The mixture was then boiled under reflux for 4 h. The mixture was then cooled to 60° C., a catalytic amount of pyridine was added and phosgene was introduced under reflux for 12 h until a clear solution was obtained. After cooling to 30° C., the product was freed from the solvent. This gave 11.6 g (98% of theory) of the title compound.

Workup

  1. temperatureunder reflux for 4 h
  2. temperatureunder reflux for 12 h until a clear solution
  3. customwas obtained
  4. temperatureAfter cooling to 30° C.

Sources & evidence

ORD record
ord-d653e7d5512a41f2878578ec6b7d9f67
Source dataset
uspto-grants-2010_06
Patent number
US07741485B2

Reaction notes

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