Hydrochloric Acid → methyl 3-[5-(2,4-dichlorophenoxy)-2-nitrophenyl]tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 2255877Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:9]=[CH:10][C:11]([N+:28]([O-:30])=[O:29])=[C:12]([N:14]2[C:19](=[O:20])[NH:18][C:17](=[O:21])[N:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15]2=[O:27])[CH:13]=1.[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[OH:39].Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[O:39][C:8]1[CH:9]=[CH:10][C:11]([N+:28]([O-:30])=[O:29])=[C:12]([N:14]2[C:19](=[O:20])[NH:18][C:17](=[O:21])[N:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15]2=[O:27])[CH:13]=1

Participants

Conditions

Temperature: 38 °C

Procedure

Potassium carbonate (1.14 g, 8.25 mmol) is added to a solution of methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.93 g, 2.74 mmol) and 2,4-dichlorophenol (0.66 g, 4.07 mmol) in N,N-dimethylformamide at 38° C. The reaction mixture is stirred at 38° C. for 3 days, cooled to room temperature and poured into 1M hydrochloric acid. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an orange oil. Column chromatography of the oil using silica gel and 30% to 40% ethyl acetate in hexanes solutions gives the title product as a yellow foam which is identified by NMR spectral analysis.

Workup

temperaturecooled to room temperature
extractionThe aqueous mixture is extracted with ethyl acetate
washwashed sequentially with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto obtain an orange oil

Sources & evidence

ORD record: ord-fba365b7bfd14f288e676c70a62cb146
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654256

Reaction notes

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