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

HRID 1517757

Reaktionsgleichung

Reaktionsgleichung von HRID 1517757
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([CH2:18][OH:19])[C:11]=2[OH:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1.[OH-].[Na+].C(S(O)=O)(N)=N.Cl>O.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][N:9]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([CH2:18][OH:19])[C:11]=3[OH:20])[N:21]=[C:4]2[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 61274Thiourea dioxideHCID 1363483072-((4-Fluoro-2-nitrophenyl)diazenyl)-6-(hydroxymethyl)-4-methoxyphenol

Produkt 1

HCID 669077462-(5-fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-6-(hydroxymethyl)-4-methoxyphenolAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 500 ml round bottom flask equipped with a magnetic stirrer, liquid addition funnel, powder addition funnel, and nitrogen inlet was added 2-((4-fluoro-2-nitrophenyl)diazenyl)-6-(hydroxymethyl)-4-methoxyphenol from Example 5 part I and 200 ml ethanol. NaOH (21.7 g, 542 mmol) pellets (97+%, A.C.S. reagent, Aldrich) were dissolved in 100 ml deionized water and approximately one-fourth of the solution was added dropwise to the reaction mixture. The mixture was subsequently heated to 80° C. and 29.3 g (271 mmol) formamidinesulfinic acid (Aldrich) and the remaining sodium hydroxide solution were concurrently added to the reaction mixture over 30 minutes. The mixture was stirred at 80° C. for 3 hours and the contents were then poured into 3 L deionized water and acidified to pH 4 using 1N HCl. The solid was collected by filtration, suspended in 300 ml methanol, and stirred for 30 minutes while cooling to below −20° C. The solid was collected by filtration and then suspended in 300 ml ethanol, cooled again to below −20° C., filtered, and then dried to afford 7.8 g (30%) of a yellow solid, which was used in the next esterification step.

Aufarbeitung

  1. customIn a 500 ml round bottom flask equipped with a magnetic stirrer, liquid addition funnel, powder addition funnel, and nitrogen inlet
  2. additionapproximately one-fourth of the solution was added dropwise to the reaction mixture
  3. additionthe contents were then poured into 3 L
  4. filtrationThe solid was collected by filtration
  5. stirringstirred for 30 minutes
  6. temperaturewhile cooling to below −20° C
  7. filtrationThe solid was collected by filtration
  8. temperaturecooled again to below −20° C.
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6ab87ebf614b40ebbfda082b3c34f1dc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232326B2

Verknüpfte Notizen

Wird geladen…