Sodium Carbonate → HCID 10847586, compound

HRID 2392634Notes

Reaction equation

[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[N+:15]([O-])([O-:17])=[O:16].[K+].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=[CH:8][C:7]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

N,N-dimethyl-N'-(2-methoxyphenyl)ethylenediamine (D18, 1.5 g, 0.0077 mole) was dissolved in 5N sulphuric acid (0.86 ml) and the water was removed in vacuo. Conc. H2SO4 (6.5 ml) was added and the mixture stirred until homogeneous, then cooled to 0° C. Potassium nitrate (1.01 g, 0.01 mole) was added portionwise, maintaining the temperature below 10° C., and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured onto ice (150 ml) and made slightly alkaline by addition of sodium carbonate. This solution was extracted into EtOAc, dried (Na2SO4) and evaporated in vacuo, to leave an orange oil. This was purified by flash column chromatography to afford the title compound as an orange oil (0.90 g, 49%)

Workup

customthe water was removed in vacuo
additionConc. H2SO4 (6.5 ml) was added
temperaturemaintaining the temperature below 10° C.
stirringthe mixture was stirred at room temperature for 4 hours
additionThe reaction mixture was poured onto ice (150 ml)
extractionThis solution was extracted into EtOAc
dry with materialdried (Na2SO4)
customevaporated in vacuo
customto leave an orange oil
customThis was purified by flash column chromatography

Sources & evidence

ORD record: ord-c13d42e17f0645e593328ae44fed75da
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801170

Reaction notes

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