5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 86687583, compound

HRID 1473526Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].CO[CH:13]=[C:14]1[C:19](=[O:20])[O:18][C:17]([CH3:22])([CH3:21])[O:16][C:15]1=[O:23]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][CH:13]=[C:14]2[C:15](=[O:23])[O:16][C:17]([CH3:21])([CH3:22])[O:18][C:19]2=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a vial charged with 3-bromo-4-methoxyaniline (1.207 g, 5.97 mmol) was added IPA (11.95 ml) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.112 g, 5.97 mmol) respectively. The mixture was heated to 90° C. for 2 hrs providing a brown solution which was cooled to room temp affording an orange precipitate which was collected by vacuum filtration affording 5-(((3-bromo-4-methoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.8 g, 5.05 mmol, 85% yield). This solid was transferred to a 5-20 ml microwave vial and 10 ml (0.5M 1,2-dichlorobenzene) was added and the mixture irradiated at 225° C. for 15 mins affording conversion to desired product according to LC-MS. To the suspension was added diethyl ether (˜5 ml) to aid in product precipitation. To precipitate was collected via vacuum filtration and washed with ether, affording a brown solid as an isomeric mixture (˜10:1) (595 mg, 39%). m/z (ESI) 256.1 (M+H)+.

Workup

customproviding a brown solution which
temperaturewas cooled to room temp
customaffording an orange precipitate which
filtrationwas collected by vacuum filtration

Sources & evidence

ORD record: ord-6bd493aa40804bcea0b1813cb4f233bf
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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