2,6-Difluorobenzoyl chloride → 5-Amino-2-(2,6-difluorophenyl)oxazole-4-carbonitrile

HRID 389709

Reaktionsgleichung

Reaktionsgleichung von HRID 389709
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][CH:13]([C:16]#[N:17])[C:14]#[N:15].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21](Cl)=[O:22]>CN1C(=O)CCC1.CCOC(C)=O.O>[NH2:15][C:14]1[O:22][C:21]([C:20]2[C:19]([F:18])=[CH:27][CH:26]=[CH:25][C:24]=2[F:28])=[N:12][C:13]=1[C:16]#[N:17]

Komponenten

6

Edukt 2

HCID 874382,6-Difluorobenzoyl chlorideHCID 563049Aminomalononitrile p-toluenesulphonate

Produkt 1

HCID 595875015-Amino-2-(2,6-difluorophenyl)oxazole-4-carbonitrileAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of aminomalononitrile p-toluenesulfonate (0.050 g, 0.2 mmol) in NMP (0.5 mL) was added 2,6-difluorobenzoyl chloride (27 ul, 0.21 mmol) and the resulting solution heated in the microwave at 120° C. for 5 minutes. The solution was diluted with EtOAc and water. The organic phase was washed with water and brine, dried over MgSO4 and the solvent removed in vacuo to afford 5-amino-2-(2,6-difluorophenyl)oxazole-4-carbonitrile (0.030 g, 0.14 mmol, 69%) as an off-white solid. 1H NMR (DMSO) δ 7.30 (2H, t), 7.61 (1H, m), 8.14 (2H, br. s). LCMS (1) Rt: 1.59 min; m/z (ES+) 222.

Aufarbeitung

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2006a793da44ad08a9582c24c1cc95e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378095B2

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