Tetrahydrofuran → Methyl 2-[2-[4-(perhydropyridazin-1-ylthiocarbonylamino)-3-fluorophenoxy-methyl]-5-methylphenoxy]propionate

HRID 482432Notes

Reaction equation

HRID 482432 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[N:24]=[C:25]=[S:26])[O:5][CH2:6][C:7]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12].I.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1.[OH-].[Na+].O1CCCC1>O>[N:28]1([C:25]([NH:24][C:23]2[CH:22]=[CH:21][C:4]([O:5][CH2:6][C:7]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:8]=3[O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:3][C:2]=2[F:1])=[S:26])[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12314334Perhydropyridazine hydroiodideHCID 18981035Methyl 2-[2-(3-fluoro-4-isothiocyanatophenoxymethyl)-5-methylphenoxy]propionate

Product 1

HCID 54069749Methyl 2-[2-[4-(perhydropyridazin-1-ylthiocarbonylamino)-3-fluorophenoxy-methyl]-5-methylphenoxy]propionateYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By the method of Example 1, Step C, of U.S. Pat. No. 4,906,281, 1.50 g (0.004 mole) of methyl 2-[2-(3-fluoro-4-isothiocyanatophenoxymethyl)-5-methyl-phenoxy]propionate and 1.07 g (0.005 mole) of perhydropyridazine monohydroiodide (prepared by the method of Example 1, Step B, of U.S. Pat. No. 4,906,281) were reacted in the presence of 0.20 g (0.0050 mole of sodium hydroxide in 40 mL of water and 10 ML of tetrahydrofuran, yielding 1.50 g of methyl 2-[2-[4-(perhydropyridazin-1-ylthiocarbonylamino)-3-fluorophenoxy-methyl]-5-methylphenoxy]propionate as a syrup. The NMR spectrum was consistent with proposed structure.

Sources & evidence

ORD record
ord-a278fd0afe234eeaaf49f442da655cd0
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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