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

HRID 909332Notes

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 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 washed with ice cold ethanol until the washings
customthe product was dried at 65° C. under vacuum

Sources & evidence

ORD record: ord-8327f6be887b4352ac64e495e5e7144e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017779B2

Reaction notes

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