Pyridine → 2-phenylethyl N-[4-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-1,3-thiazol-2-yl]carbamate

HRID 520256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520256
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[C:11]#[N:12])[N:6]=1.N1C=CC=CC=1.[C:25]1([CH2:31][CH2:32][O:33][C:34](Cl)=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[C:11](/[C:10](=[N:9]\[O:8][CH2:7][C:5]1[N:6]=[C:2]([NH:1][C:34](=[O:35])[O:33][CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:3][CH:4]=1)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:12]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 159175902-Phenylethyl chloroformateHCID 89443882(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanide

Produkt 1

HCID 896557582-phenylethyl N-[4-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-1,3-thiazol-2-yl]carbamateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (1 g, 3.87 mmol, 1 eq.) in dry dichloromethane (15 ml) at room temperature was added pyridine (0.38 ml, 4.65 mmol, 1.2 eq). After stirring for 15 min at room temperature 2-phenylethylcarbonochloridate (858 mg, 4.65 mmol, 1.2 eq) was added and stirring was allowed during 5 h. The reaction was quenched by addition of water and concentrated to dryness. The residue was taken in DCM (5 mL) and 5 ml of 1N NaOH was added. The layers were separated and the organic phase was dried over MgSO4 then concentrated to give 2-phenylethyl {4-[({[(Z)-cyano(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate (1.2 g, 55% yield) which was used in the next step without further purification.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched by addition of water
  3. concentrationconcentrated to dryness
  4. addition5 ml of 1N NaOH was added
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationthen concentrated

Quellen und Nachweise

ORD-Eintrag
ord-98a606b9daef4228a3874a763e365694
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326515B2

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