Ethyl bromoacetate → ethyl 2,4-dichloro-5-[4-methyl-1,2,4-triazine-3,5(2H,4H)-dione-2-yl]phenoxyacetate

HRID 35424Notes

Reaction equation

HRID 35424 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:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CC(C)=O>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:10]2[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[CH:12]=[N:11]2)=[CH:4][C:5]=1[O:9][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 142769422-(2,4-dichloro-5-hydroxyphenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione2×

Product 1

HCID 1214846ethyl 2,4-dichloro-5-[4-methyl-1,2,4-triazine-3,5(2H,4H)-dione-2-yl]phenoxyacetateYield 75.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to Example II, Step C, the reaction of 0.86 g (0.0030 mole) of 2-(2,4-dichloro-5-hydroxyphenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione (Compound 9, Example III H) with 0.62 g (0.0045 mole) of potassium carbonate and 0.75 g (0.0045 mole) of ethyl bromoacetate in 10 mL of acetone produced an oil. The oil crystallized upon treatment with heptane to yield 0.85 g of ethyl 2,4-dichloro-5-[4-methyl-1,2,4-triazine-3,5(2H,4H)-dione-2-yl]phenoxyacetate (mp 115°-117° C.), Compound 22 in the tables.

Workup

  1. customproduced an oil
  2. customThe oil crystallized upon treatment with heptane

Sources & evidence

ORD record
ord-3102b665ce0144b59bb76da412e2ca35
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Reaction notes

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