Methanol → HCID 57566615, Verbindung

HRID 217152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217152
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[N+:35]([O-])([OH:37])=[O:36].CO>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:35]([O-:37])=[O:36])[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 944Nitric AcidHCID 9845Trifluoroacetic anhydrideHCID 57566613HCID 57566613, Verbindung

Produkt 1

HCID 57566615HCID 57566615, VerbindungAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of N[4-bromo-2-(3-fluoro-pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide (6.45 grams, 18.4 mmoles) in TFA (100 mL) and TFAA (25.5 mL, 183.6 mmole), at 0° C., was added a TFA solution (30 mL) of 90% fuming nitric acid (2.46 mL, 55.1 mmoles) over a 45 minute period. The mixture was then stirred at 0° C. for a total of 4 hours. The crude reaction (now homogenous) was poured into ice producing a pasty mass. The mixture was diluted to 500 mL total volume with water, treated with 50 mL of methanol, and vigorously stirred for 12 hours. The resulting solids were filtered, washed with copious amounts of water, then dried in vacuo at 50° C. to afford the title compound (6.1 grams, 82% yield) as a tan powder.

Aufarbeitung

  1. customThe crude reaction (now homogenous)
  2. additionwas poured into ice producing a pasty mass
  3. stirringvigorously stirred for 12 hours
  4. filtrationThe resulting solids were filtered
  5. washwashed with copious amounts of water
  6. customdried in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-3328d918fcf84d7986acc27be07e5fd1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193352B2

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