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

HRID 2389815Notes

Reaction equation

HRID 2389815 reaction equation
[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]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470153HCID 178470153, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-025099723a3c47efa7f399b72ebe39de
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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