Iodoacetamide → [2,4-dichloro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]acetamide

HRID 1382157Notes

Reaction equation

HRID 1382157 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]([F:19])[F:18])=[N:11]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:27][C:28]([NH2:30])=[O:29]>CC(C)=O>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:10]2[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]([F:18])[F:19])=[N:11]2)=[CH:4][C:5]=1[O:9][CH2:27][C:28]([NH2:30])=[O:29]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 11430Potassium CarbonateHCID 143924871-(2,4-dichloro-5-hydroxyphenyl)-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one

Product 1

HCID 14853675[2,4-dichloro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]acetamideYield 817.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to Example 1, the reaction of 0.72 g (0.00023 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-3-difluromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one, 0.32 g (0.00023 mole) of potassium carbonate, and 0.47 g (0.00025 mole) of iodoacetamide in 5 mL of acetone produced 0.69 g of [2,4-dichloro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]acetamide (mp 190°-193.5° C).

Sources & evidence

ORD record
ord-4a89244c227f45a29aa96dfba627a7f1
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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