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

HRID 2389815

Reaktionsgleichung

[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

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

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

Quellen und Nachweise

ORD-Eintrag: ord-025099723a3c47efa7f399b72ebe39de
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08273752B2

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