Trichloroisocyanuric Acid → HCID 57912300, Verbindung

HRID 1499328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499328
[C:1]([O-:4])(O)=[O:2].[Na+].[N+:6]([C:9]1[C:14]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=1CO)([O-:8])=[O:7].[Na+].[Br-].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1.CC(O)C>[Si:17]([O:16][CH2:15][C:14]1[C:9]([N+:6]([O-:8])=[O:7])=[C:10]([CH:11]=[CH:12][CH:13]=1)[C:1]([OH:4])=[O:2])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Komponenten

8

Edukt 4

HCID 6909Trichloroisocyanuric AcidHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 57912293HCID 57912293, Verbindung

Produkt 1

HCID 57912300HCID 57912300, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2724126TempoKatalysatorHCID 180AcetoneLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

An aqueous solution of 15% NaHCO3 (18 mL) was added to a stirring solution of Compound 9 (1.80 g, 2.69 mmol) in acetone (60 mL) at 0° C. NaBr (133 mg, 1.29 mmol) and TEMPO (18.9 mg, 0.121 mmol) were then added followed by the slow addition of trichloroisocyanuric acid (2.81 g, 12.1 mmol). The resulting solution was allowed to warm to room temperature and stirring for 1 d after which time 2-propanol (3.63 mL) was added. The mixture was filtered over Celite, concentrated on a rotary evaporator, dissolved in 18 mL of saturated Na2CO3, washed with EtOAc (3×10 mL), acidified with 1 M HCl, and extracted with ethyl acetate (3×50 mL). The resulting organics were dried over Na2SO4, filtered, concentrated on a rotary evaporator and purified by silica gel chromatography (10% MeOH:CH2Cl2) to yield Compound 10 (1.05 g, 56%) as a white solid.

Aufarbeitung

  1. additionwas added
  2. filtrationThe mixture was filtered over Celite
  3. concentrationconcentrated on a rotary evaporator
  4. dissolutiondissolved in 18 mL of saturated Na2CO3
  5. washwashed with EtOAc (3×10 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe resulting organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. custompurified by silica gel chromatography (10% MeOH:CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-411387c1951a4c73bad69464089e4eb3
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200097B2

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