Sulfuryl chloride → HCID 21274220, compound

HRID 1382141Notes

Reaction equation

HRID 1382141 reaction equation
[F:1][CH:2]([F:19])[N:3]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([O:16][CH3:17])[CH:10]=2)[N:5]=[C:4]1[CH3:18].S(Cl)([Cl:23])(=O)=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:23][C:14]1[CH:13]=[C:12]([CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[N:6]1[C:7](=[O:8])[N:3]([CH:2]([F:1])[F:19])[C:4]([CH3:18])=[N:5]1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21274224HCID 21274224, compound

Product 1

HCID 21274220HCID 21274220, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 15.0 g (0.056 mole) of 4-difluoromethyl-4,5-dihydro-1-(4-methyl-3-methoxyphenyl)-3-methyl-1,2,4-triazol-5(1H)-one and 7.5 g (0.056 mole) of sulfuryl chloride in 100 mL of chloroform was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure to leave a residue. This residue was dissolved in methylene chloride and washed with an aqueous 10% sodium hydroxide solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 16.5 g of 1-(2-chloro-4-methyl-5-methoxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto leave a residue
  3. washwashed with an aqueous 10% sodium hydroxide solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3db7936332f34793a9beedc2253bda4a
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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