2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-[(5-Fluoro-2-propoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 238322Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11]([O-])([O-])OC.[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH3:27])=[C:21]([CH:23]=1)[NH2:22]>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH3:27])=[C:21]([NH:22][CH:11]=[C:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])[CH:23]=1

Participants

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

HCID 261896335-Fluoro-2-propoxyaniline

HCID 53629101Methylorthoformate2×

Product 1

HCID 669172145-[(5-Fluoro-2-propoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 93%

Conditions

Temperature: 50 °C

Procedure

Meldrum's acid (5.29 g, 36.7 mmol) was added to methyl orthoformate (31 ml), and the mixture was stirred for 2 hours while heating under reflux. The resulting mixture was cooled to 50° C., and 5-fluoro-2-propoxyaniline (4.28 g, 25.3 mmol) and methyl orthoformate (3 ml) were added thereto. The resulting mixture was stirred for 6 hours while heating under reflux. The resulting reaction mixture was then cooled to room temperature, and concentrated under reduced pressure. The residue was recrystallized from methanol to thereby obtain 7.61 g of powdery pale brown 5-[(5-fluoro-2-propoxyphenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (yield: 93%).

Workup

temperaturewhile heating
temperatureunder reflux
stirringThe resulting mixture was stirred for 6 hours
temperaturewhile heating
temperatureunder reflux
customThe resulting reaction mixture
temperaturewas then cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-995e365a870045a9a83363c590816e85
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642619B2

Reaction notes

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