p-Toluenesulfonyl isocyanate → HCID 21274226, compound

HRID 1382152Notes

Reaction equation

HRID 1382152 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH:21]([F:23])[F:22])[C:17]([CH3:24])=[N:16]2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6](O)=[O:7].[C:25]1([CH3:37])[CH:30]=[CH:29][C:28]([S:31]([N:34]=C=O)(=[O:33])=[O:32])=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:37][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:34][C:6](=[O:7])[CH:5]([O:4][C:3]2[CH:10]=[C:11]([N:15]3[C:19](=[O:20])[N:18]([CH:21]([F:23])[F:22])[C:17]([CH3:24])=[N:16]3)[C:12]([F:14])=[CH:13][C:2]=2[Cl:1])[CH3:9])(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 13769460HCID 13769460, compound

Product 1

HCID 21274226HCID 21274226, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of 0.78 g (0.0021 mole) of 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid, 0.42 g (0.0021 mole) of p-toluenesulfonyl isocyanate and 0.05 g (0.0004 mole) of 4-dimethylaminopyridine in 50 mL of toluene was heated at reflux for approximately 18 hours. The mixture was allowed to cool to room temperature and was stirred for 24 hours. The solvent was removed by evaporation at reduced pressure to leave a residue. This residue was purified by column chromatography on silica gel, eluting with toluene:ethyl acetate (1:1). The appropriate fractions were combined and evaporated under reduced pressure to yield 0.7 g of N-(4-methylphenylsulfonyl)-2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionamide as a solid, Compound C10.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. customThe solvent was removed by evaporation at reduced pressure
  4. customto leave a residue
  5. customThis residue was purified by column chromatography on silica gel
  6. washeluting with toluene:ethyl acetate (1:1)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7563adcdfbf847d3a0514bc19164dd36
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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