Potassium Carbonate → Methyl 2-[2-[4-(4-methyl-1,2,4-triazine-3,5-dion-2-yl)-3-fluorophenoxymethyl]-5-methylphenoxy]propionate

HRID 482415Notes

Reaction equation

HRID 482415 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[CH:10]=[N:9]2)=[C:4]([F:17])[CH:3]=1.Cl[CH2:19][C:20]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:21]=1[O:22][CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][N:12]1[C:11](=[O:16])[CH:10]=[N:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:19][C:20]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:21]=3[O:22][CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:3][C:4]=2[F:17])[C:13]1=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15765398Methyl 2-(2-chloromethyl-5-methylphenoxy)propionateHCID 189810672-(4-Hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione

Product 1

HCID 3502945Methyl 2-[2-[4-(4-methyl-1,2,4-triazine-3,5-dion-2-yl)-3-fluorophenoxymethyl]-5-methylphenoxy]propionateYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of Example 1, Step I, 0.47 g (0.002 mole) of 2-(4-hydroxy-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5-dione and 0.73 g (0.003 mole) of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate were reacted in the presence of 0.41 g (0.003 mole) of anhydrous potassium carbonate in 30 mL of N,N-dimethylformamide, yielding 0.70 g of methyl 2-[2-[4-(4-methyl-1,2,4-triazine-3,5-dion-2-yl)-3-fluorophenoxymethyl]-5-methylphenoxy]propionate as a syrup. The IR and NMR spectra were consistent with the proposed structure. NMR: 1.60 (d, 3H, JHH=8.0 Hz); 2.30 (s, 3H); 3.40 (s, 3H); 3.78 (s, 3H); 4.84 (q, 1H, JHH=8.0 Hz); 5.18 (dd, 2H, JHH=10 Hz); 6.58 (s, 1H); 6.8-7.3 (m, 5H); 7.54 (s, 1H).

Sources & evidence

ORD record
ord-e26f110df58e49ac9cf4be14faeb1360
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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