Dimethylamine → 2,6-Dibromo-3,5-dihydroxy-4[(dimethylamino) methylene]-benzoic Acid

HRID 1692613Notes

Reaction equation

C=O.[CH2:3](O)C.[CH3:6][NH:7][CH3:8].[Br:9][C:10]1[C:18]([OH:19])=[CH:17][C:16]([OH:20])=[C:15]([Br:21])[C:11]=1[C:12]([OH:14])=[O:13]>C(O)(=O)C>[Br:9][C:10]1[CH:18]([OH:19])[C:17](=[CH:6][N:7]([CH3:3])[CH3:8])[C:16]([OH:20])=[C:15]([Br:21])[C:11]=1[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred mixture of 37% of aqueous formaldehyde solution (2 mmol), absolute ethanol (0.4 mL), and glacial acetic acid (0.8 mL) was added 40% of aqueous dimethylamine (2 mmol) solution under ice bath (25° C.). The ice bath was removed and 2,6-Dibromo-3,5-dihydroxybenzoic Acid (1 mmol) was added over a period of 2 min. The mixture became darkened, and after 5 min a white solid began to appear. The mixture was stirred at 25° C. for 24 h and then at 0° C. for 2 h to allow complete precipitation of product. The precipitate was washed with ice-cold acetone (2×0.5 mL), dried under oil pump to give 2,6-Dibromo-3,5-dihydroxy-4[(dimethylamino) methylene]-benzoic Acid (98%): 1H NMR (DMSO-d6) δ 3.92 (s, 2H), 2.41 (s, 6H).

Workup

customThe ice bath was removed
waitat 0° C. for 2 h to allow complete
customprecipitation of product
washThe precipitate was washed with ice-cold acetone (2×0.5 mL)
customdried under oil pump

Sources & evidence

ORD record: ord-e24b4132c5064bc1b92696f2c0186306
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158623B2

Reaction notes

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