Thionyl Chloride → HCID 15022944, compound

HRID 893523Notes

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

Conditions

Temperature: 120 °C

Procedure

In a manner similar to Example 4, 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 2) 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 25 of Table 1.

Workup

customproduced a residue
temperaturewas cooled
customa resultant precipitate was removed by filtration
washThe filtrate was washed with water
dry with materialThe organic phase was dried over anhydrous magnesium sulfate
filtrationfiltered
customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record: ord-5d509fe4942245409b2c8264e9f67c59
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05125958

Reaction notes

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