3-Bromoaniline → 5-((3-Bromophenylamino)methylene)-2,2-di-methyl-1,3-dioxane-4,6-dione

HRID 1818096Notes

Reaction equation

[CH:1](OCC)(OCC)OCC.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>C(O)C>[Br:21][C:22]1[CH:23]=[C:24]([NH:25][CH:1]=[C:16]2[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:15])[CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of triethyl orthoformate (154 grams (g), 1.04 moles (mol) and Meldrum's acid (142 g, 0.983 mol) was heated to 55° C. for 4 hours (h). After cooling to 50° C., a solution of 3-bromoaniline (162.6 g, 0.945 mol) in ethanol (300 mL) was added such that the temperature of the reaction was maintained between 50-55° C. After half of the 3-bromoaniline had been added, stirring became difficult due to the formation of solids, so more ethanol (1 liter (L)) was added to facilitate stirring. Upon complete addition, the reaction was cooled to room temperature (RT), and the solids were collected by filtration. The filter cake was washed with ice cold ethanol until the washings were nearly colorless, and the product was dried at 65° C. under vacuum to afford 287 g of 5-[(3-bromophenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione as an off-white solid.

Workup

temperatureAfter cooling to 50° C.
temperaturewas maintained between 50-55° C
additionwas added
stirringto facilitate stirring
additionUpon complete addition
temperaturethe reaction was cooled to room temperature (RT)
filtrationthe solids were collected by filtration
washThe filter cake was washed with ice cold ethanol until the washings
customthe product was dried at 65° C. under vacuum

Sources & evidence

ORD record: ord-28b09c4afc1e4630898aa9209f0cce28
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598382B2

Reaction notes

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