Hydrochloric Acid → 2-(hydroxymethyl)-4-methoxy-6-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenol

HRID 1691511

Reaktionsgleichung

[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[N+:21]([O-])=O)[C:4]=1[OH:24].[OH-].[Na+].C(S(O)=O)(N)=N.Cl>C(O)C.O>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]3=[N:21]2)[C:4]=1[OH:24]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

In a 500 ml round bottom 3-neck flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet was added 2-(hydroxymethyl)-4-methoxy-6-((4-methoxy-2-nitrophenyl)diazenyl)phenol and 200 ml absolute ethanol (Pharmco Products, Brookfield, Conn.). NaOH pellets, 97% (Aldrich, 16.8 g, 420 mmol) were dissolved in 80 ml deionized water and approximately one-fourth of the solution was added dropwise to the azo mixture. The reaction mixture was heated to 80° C. and 22.6 g (209 mmol) formamidinesulfinic acid (Aldrich) and the remaining NaOH solution were added concurrently to the azo mixture over 0.5 hr. The mixture was heated at 80° C. for 3 hours, poured into 3.5 L water, and acidified to pH 4-5 with conc. HCl (J. T. Baker). The crude product was recrystallizsed from ethanol and then collected and vacuum dried (0.1 mm Hg) at 50° C. for 72 hours to give 7 g (27%) of a light yellow solid.

Aufarbeitung

customIn a 500 ml round bottom 3-neck flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet
temperatureThe mixture was heated at 80° C. for 3 hours
customcollected
customvacuum dried (0.1 mm Hg) at 50° C. for 72 hours

Quellen und Nachweise

ORD-Eintrag: ord-11b641e8d8a842e1ad977b8a526d1dc7
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08153703B2

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