Methanol → HCID 57566615, Verbindung

HRID 563966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563966
[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-8d799a0f111f4e9fb1ab45b34c2a1004
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067606B2

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