HCID 19912217, compound → HCID 19912206, compound

HRID 1090994Notes

Reaction equation

HRID 1090994 reaction equation
N[C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[C:8]([Cl:24])=[CH:9][C:10]([Cl:23])=[C:11]([N:13]3[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]3)[CH:12]=2)=[C:4]([Cl:27])[CH:3]=1.N([O-])=[O:29].[Na+]>S(=O)(=O)(O)O.O.C1(C)C(C)=CC=CC=1.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:23][C:10]1[CH:9]=[C:8]([Cl:24])[C:7]([O:6][C:5]2[CH:25]=[CH:26][C:2]([OH:29])=[CH:3][C:4]=2[Cl:27])=[CH:12][C:11]=1[N:13]1[C:17](=[O:18])[N:16]([CH:19]([F:20])[F:21])[C:15]([CH3:22])=[N:14]1

Participants

7

Reactant 2

HCID 19912217HCID 19912217, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19912206HCID 19912206, compoundYield 32%

Reagents, catalysts & solvents 4

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 7237O-XyleneSolvent

Procedure

In a manner similar to Step C of Example 1, 8.10 g (0.0186 mole) of 1-[5-(4-amino-2-chlorophenoxy)-2,4-dichlorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 60 ml of concentrated sulfuric acid was reacted with a solution of 1.30 g (0.019 mole) of sodium nitrite in 10 ml of water. Subsequent reaction of this mixture with a refluxing solution of 150.0 g (0.60 mole) of copper (II) sulfate pentahydrate in 150 ml of water and 1.50 ml of xylene yielded 2.6 g of 1-[2,4-dichloro-5-(2-chloro-4-hydroxyphenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, compound 181 of Table 1.

Sources & evidence

ORD record
ord-12bf3e4da1f04c4b98e3e9fe57852d5a
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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