3-(Trifluoromethoxy)aniline → HCID 67338962, Verbindung

HRID 2092300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092300
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[N:3]=1.[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1>CC(O)C>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:14])[N:3]=[C:2]2[NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:16]([F:15])([F:25])[F:26])[CH:19]=1

Komponenten

4

Edukt 2

HCID 737533-(Trifluoromethoxy)anilineHCID 584664654-Chloro-8-iodo-2,7-dimethylquinazoline

Produkt 1

HCID 67338962HCID 67338962, VerbindungAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

4-Chloro-8-iodo-2,7-dimethylquinazoline (0.30 g, 0.94 mmol) and 3-(trifluoromethoxy)benzenamine (0.20 g, 1.1 mmol) were placed in a microwave vial containing 3 mL of IPA. The vial was capped and heated in a microwave reactor at 170° C. for 10 min. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was dried with sodium sulfate, concentrated and purified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes to give a 8-iodo-2,7-dimethyl-N-(3-(trifluoromethoxy)phenyl)quinazolin-4-amine (0.32 g, 74%) as an off-white solid. MS (M+H)+ 460.

Aufarbeitung

  1. customThe vial was capped
  2. concentrationThe mixture was concentrated in vacuo
  3. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-35edadf261a14e75963cee1bad42e992
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440674B2

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