Potassium Carbonate → Methyl 2-[2-[3-fluoro-4[1-(1-methylethyl)imidazolidin-2,4-dion-3-yl]phenoxymethyl]-5-chloro-phenoxy]propionate

HRID 482396Notes

Reaction equation

HRID 482396 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[F:17])[C:5]1=[O:18])[CH3:3].Cl[CH2:20][C:21]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:22]=1[O:23][CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+]>>[F:17][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:10]=1[N:6]1[C:7](=[O:9])[CH2:8][N:4]([CH:2]([CH3:1])[CH3:3])[C:5]1=[O:18])[O:16][CH2:20][C:21]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:22]=1[O:23][CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 189810733-(2-Fluoro-4-hydroxyphenyl)-1-isopropyl-2,4-imidazolidinedioneHCID 53768369Methyl 2-(2-chloromethyl-5-chlorophenoxy)propionate

Product 1

HCID 18981036Methyl 2-[2-[3-fluoro-4[1-(1-methylethyl)imidazolidin-2,4-dion-3-yl]phenoxymethyl]-5-chloro-phenoxy]propionateYield 90.5%

Procedure

By the method of Example 1, Step I, 0.60 g (0.0024 mole) of 1-(1-methylethyl)-3-(2-fluoro-4-hydroxyphenyl)imidazolidin-2,4-dione, 1.24 g (0.0048 mole) of methyl 2-(2-chloromethyl-5-chlorophenoxy)propionate (Example 2, Step E), and 0.5 g (0.0036 mole) of potassium carbonate were reacted in 25 mL of 2-utanone. After purification, 1.04 g of methyl 2-[2-[3-fluoro-4[1-(1-methylethyl)imidazolidin-2,4-dion-3-yl]phenoxymethyl]-5-chloro-phenoxy]propionate was isolated as a yellow oil. The NMR and IR spectra were consistent with the proposed structure. NMR: 1.24 (d, 6H, JHH=8 Hz); 1.64 (d, 3H, JHH=8 Hz); 3.68 (s, 3H); 3.96 (s, 1H); 4.44 (septet, 1H, JHH=8.0 Hz); 5.04 (q, 1H, JHH=8.0 Hz); 5.24 (s, 2H); 6.80-7.34 (m, 5H).

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-e07dea1067fa433096380dc4098f3436
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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