Potassium Carbonate → methyl 2-[3-[4-(4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl)-3-fluorophenoxymethyl]phenoxy]propionate

HRID 257393Notes

Reaction equation

HRID 257393 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH:15]([F:17])[F:16])[C:11]([CH3:18])=[N:10]1.Cl[CH2:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[O:24][CH:25]([CH3:30])[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:16][CH:15]([F:17])[N:12]1[C:13](=[O:14])[N:9]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:20][C:21]3[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=3)[O:24][CH:25]([CH3:30])[C:26]([O:28][CH3:29])=[O:27])=[CH:7][C:2]=2[F:1])[N:10]=[C:11]1[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142799031-(2-Fluoro-4-hydroxyphenyl)-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-oneHCID 18981053Methyl 2-(3-chloromethylphenoxy)propionate

Product 1

HCID 18981026methyl 2-[3-[4-(4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl)-3-fluorophenoxymethyl]phenoxy]propionateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of Example 1, Step K, 1.0 g (0.0038 mole) of 1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one (Example 1, Step F) and 1.72 g (0.0076 mole) of methyl 2-(3-chloromethylphenoxy)propionate were reacted in the presence of 0.79 g (0.0057 mole) of anhydrous potassium carbonate in 25 mL of N,N-dimethylformamide, yielding 1.54 g of methyl 2-[3-[4-(4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl)-3-fluorophenoxymethyl]phenoxy]propionate. The NMR and IR spectra were consistent with the proposed structure. NMR: 1.60 (d, 3H, JHH =8.0 Hz); 2.44 (s, 3H); 3.76 (s, 3H); 4.78 (q, 1H, JHH =8.0 Hz); 5.04 (s, 2H); 6.76-7.38 (m, 8H).

Sources & evidence

ORD record
ord-60ad23da51064b88857b7ca02a8e4a17
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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