Oxalyl chloride → Ethyl 5-(4-fluoro-2-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58648
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:22][C:23](=[N:29]O)[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[O:11][N:29]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:22]=2)=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27375922-[4-Fluoro-2-(trifluoromethyl)phenyl]acetic acidHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Produkt 1

HCID 66831832Ethyl 5-(4-fluoro-2-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylateAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

This compound was prepared according to general method 2 with (step I) 2-(4-fluoro-2-(trifluoromethyl)phenyl)acetic acid (0.420 g; 1.89 mmol) and oxalyl chloride (0.176 mL; 2.08 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.250 g; 1.89 mmol) and N,N diisopropylethylamine (0.527 mL; 3.03 mmol) in dichloromethane (10 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.063 g (10%) of ethyl 5-(4-fluoro-2-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Aufarbeitung

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-db5b2994af784b89969d97e1c4b653ef
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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