2-Chloro-1,3-thiazole-5-carbaldehyde → N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine

HRID 1502587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502587
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:14][C:15]1[S:16][C:17]([CH:20]=O)=[CH:18][N:19]=1>ClCCl>[Cl:14][C:15]1[S:16][C:17]([CH:20]=[N:1][C:2]2[C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:18][N:19]=1

Komponenten

4

Edukt 2

HCID 14797652-Chloro-1,3-thiazole-5-carbaldehydeHCID 27627953-Phenylpyridin-2-amine2×

Produkt 1

HCID 66973405N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Amino-3-phenylpyridine (i.e. the product of Step A, 0.342 g, 2.01 mmol) was added to 2-chloro-1,3-thiazole-5-carbaldehyde (0.296 g, 2.01 mmol) in dichloromethane (10 mL) at room temperature. The suspension was stirred for 10 min and then concentrated to dryness under vacuum. The resulting residue was heated to 90° C. for 20 min on a rotory evaporator with a non-returning bump trap to facilitate water removal. The residual yellow solid was again dissolved in dichloromethane (10 mL) and heated to 90° C. on a rotory evaporator for an additional 20 min. At this time the yellow solid was checked by NMR to verify reaction completion. The title compound was obtained as a yellow solid and used in the next step without further purification.

Aufarbeitung

  1. concentrationconcentrated to dryness under vacuum
  2. customwater removal
  3. dissolutionThe residual yellow solid was again dissolved in dichloromethane (10 mL)
  4. temperatureheated to 90° C. on a rotory evaporator for an additional 20 min
  5. customreaction completion

Quellen und Nachweise

ORD-Eintrag
ord-bf447b33aeba4f9ba5f71fe98f1b47f9
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09210932B2

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