Oxalyl chloride → Ethyl 5-(2,4-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58602

Reaktionsgleichung

Reaktionsgleichung von HRID 58602
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20](=[N:26]O)[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[O:12][N:26]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1235812,4-Difluorophenylacetic acidHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Produkt 1

HCID 66831972Ethyl 5-(2,4-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

This compound was prepared according to general method 2 with (step I) 2-(2,4-difluorophenyl)acetic acid (0.651 g; 3.78 mmol) and oxalyl chloride (0.352 mL; 4.16 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (6 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 0.372 g (37%) of the title compound 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-cabe49f389044f15b5c5932ae2786501
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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