Methyl iodide → Methyl 2-fluoro-4-[3-(methylthio)-1,2,4-triazin-6-yl]benzoate

HRID 500137Notes

Reaction equation

C(O[CH:4](OCC)[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([F:17])[CH:8]=1)=O)C.[NH2:21][NH:22][C:23]([NH2:25])=[S:24].O.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1.CI>C(O)C>[F:17][C:9]1[CH:8]=[C:7]([C:5]2[N:21]=[N:22][C:23]([S:24][CH3:27])=[N:25][CH:4]=2)[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl 4-(diethoxyacetyl)-2-fluorobenzoate (3.0 g, 0.01 mol) was dissolved in ethanol (30 mL). Thiosemicarbazide (1.2 g, 0.013 mol) and p-toluenesulfonic acid monohydrate (100 mg) were added to the reaction mixture. The reaction mixture was heated at 90° C. for 2 h. After cooling, the reaction mixture to ambient temperature methyl iodide (3 mL, 0.05 mol) was added. The reaction mixture was stirred at RT for 2 h, and then concentrated under reduced pressure. The residue was dissolved in acetic acid (50 mL), and heated at 60° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in methanol and the precipitate was collected by filtration and dried under reduced pressure to give the desired product. (1.2 g, 41%).

Workup

temperatureAfter cooling
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in acetic acid (50 mL)
temperatureheated at 60° C. for 2 h
concentrationThe reaction mixture was concentrated under reduced pressure
filtrationthe precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-833f8d89948b4956a4d1fdfb46cbff42
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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