Phosphorus oxychloride → Ethyl-5-chloro-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxylate

HRID 2171549

Reaktionsgleichung

Reaktionsgleichung von HRID 2171549
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13](O)[N:12]2[N:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=[C:11]2[CH:10]=1.P(Cl)(Cl)([Cl:26])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH2:22]([O:21][C:19]([C:17]1[N:18]=[C:11]2[N:12]([C:13]([Cl:26])=[N:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[CH:10]2)[N:16]=1)=[O:20])[CH3:23]

Komponenten

5

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178470153HCID 178470153, Verbindung

Produkt 1

HCID 59313032Ethyl-5-chloro-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1311 mg (3.7 mmol) of ethyl 7-(2,4-dichlorophenyl)-5-hydroxy[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxylate (Example 132A) are introduced into phosphoryl chloride (15 ml), 2.54 g (11.1 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 12 h. The reaction mixture is slowly poured, while stirring vigorously, into saturated sodium bicarbonate solution (150 ml) and ice, and solid sodium bicarbonate (approx. 10 g) is added until a pH of 8 is reached. The solid is filtered off with suction. 635 mg (93% of theory) of the product are obtained.

Aufarbeitung

  1. additionare added
  2. additionThe reaction mixture is slowly poured
  3. additionis added until a pH of 8
  4. filtrationThe solid is filtered off with suction
  5. custom635 mg (93% of theory) of the product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-2fec547005e9439b8d5c9b405fc9e9fd
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051323B2

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