Methyl iodide → 2-[2,4-Dichloro-5-(1-methylethoxy)phenyl]-4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione

HRID 35423Notes

Reaction equation

HRID 35423 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:18](=[O:19])[N:17]([CH2:20]C=C)[C:16](=[O:23])[C:15]([CH3:24])=[N:14]1.BrCC=C.IC.ClC1C(OC(C)C)=CC(N2C(=O)N(CCCF)C(=O)C=N2)=C(F)C=1.ClC1C(OC(C)C)=CC(N2C(=O)NC(=O)C=N2)=C(F)C=1.ClCCCF>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:18](=[O:19])[N:17]([CH3:20])[C:16](=[O:23])[C:15]([CH3:24])=[N:14]1

Participants

7

Reactant 6

HCID 6328Methyl iodideHCID 7841Allyl bromideHCID 118293711-Chloro-3-fluoropropaneHCID 142769482-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-4-(2-propenyl)-1,2,4-triazine-3,5(2H,4H)-dioneHCID 142769702-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-4-(3-fluoropropyl)-1,2,4-triazine-3,5(2H,4H)-dioneHCID 14747824HCID 14747824, compound

Product 1

HCID 147478302-[2,4-Dichloro-5-(1-methylethoxy)phenyl]-4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione

Procedure

Compound 16, 2-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-4-(2-propenyl)-1,2,4-triazine-3,5(2H,4H)-dione, was also prepared by the method of Example IV using 3-bromo-1-propene rather than iodomethane in Step D. Similarly, Compound 50, 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-4-(3-fluoropropyl)-1,2,4-triazine-3,5(2H,4H)-dione, was prepared by treating Compound 17 (Example II D) with 1-chloro-3-fluoropropane.

Sources & evidence

ORD record
ord-a8a4e6b860b74743ade814dcfb47518e
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Reaction notes

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