Thionyl Chloride → HCID 15022944, compound

HRID 1087362Notes

Reaction equation

HRID 1087362 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([Cl:23])=[CH:9][C:8]=1[Cl:24])[C:3](O)=[O:4].S(Cl)(Cl)=O.[CH3:29][S:30]([NH2:33])(=[O:32])=[O:31]>C(Cl)Cl>[CH3:29][S:30]([NH:33][C:3](=[O:4])[CH:2]([Cl:1])[CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([Cl:23])=[CH:9][C:8]=1[Cl:24])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 72879MethanesulfonamideHCID 15022941HCID 15022941, compound2×

Product 1

HCID 15022944HCID 15022944, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

In a manner similar to Example 7, the reaction of 0.50 g (0.0013 mole) of 2-chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionic acid (Compound A2) with 5 mL of thionyl chloride produced a residue. To this residue was added 0.50 g (0.0052 mole) of methanesulfonamide. The mixture was stirred and heated at 120° C. for two hours. The mixture was cooled, diluted with methylene chloride, and a resultant precipitate was removed by filtration. The filtrate was washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to give 0.21 g of N-methylsulfonyl-2-chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionamide as a foam, Compound A25 of Table 1A.

Workup

  1. customproduced a residue
  2. temperatureThe mixture was cooled
  3. customa resultant precipitate was removed by filtration
  4. washThe filtrate was washed with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e29bf3d1ce4407791cc8a77989a37b5
Source dataset
uspto-grants-1991_07
Patent number
US05035740

Reaction notes

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