Potassium Carbonate → N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)sulfonyl-2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionamide

HRID 1252347Notes

Reaction equation

HRID 1252347 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH:15]([F:17])[F:16])[C:11]([CH3:18])=[N:10]2)=[C:4]([F:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1([CH3:45])[CH2:31][C:30]2[CH:32]=[C:33]([S:36]([NH:39][C:40](=[O:44])[CH:41](Br)[CH3:42])(=[O:38])=[O:37])[CH:34]=[CH:35][C:29]=2[O:28]1>CC(C)=O>[CH3:45][C:27]1([CH3:26])[CH2:31][C:30]2[CH:32]=[C:33]([S:36]([NH:39][C:40](=[O:44])[CH:41]([O:8][C:7]3[CH:6]=[C:5]([N:9]4[C:13](=[O:14])[N:12]([CH:15]([F:16])[F:17])[C:11]([CH3:18])=[N:10]4)[C:4]([F:19])=[CH:3][C:2]=3[Cl:1])[CH3:42])(=[O:38])=[O:37])[CH:34]=[CH:35][C:29]=2[O:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137694562-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 15611041N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)sulfonyl-2-bromopropionamide

Product 1

HCID 20139698N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)sulfonyl-2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to Step D of Example 9, the reaction of 0.5 g (0.0017 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one with 0.7 g (0.0051 mole) of potassium carbonate and 0.62 g (0.0017 mole) of N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)sulfonyl-2-bromopropionamide in 35 mL of acetone produced 0.89 g of N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)sulfonyl-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.

Sources & evidence

ORD record
ord-3f19dabb3baa4d63b7fd21df192cc445
Source dataset
uspto-grants-1988_05
Patent number
US04743291

Reaction notes

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