Phosphorus oxychloride → 5-Chloro-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

HRID 2389820Notes

Reaction equation

HRID 2389820 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13](O)[N:12]3[N:16]=[CH:17][N:18]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:23])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:23][C:13]1[N:12]2[N:16]=[CH:17][N:18]=[C:11]2[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:19])[F:1])=[CH:4][CH:5]=2)[N:14]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517472HCID 178517472, compound

Product 1

HCID 593130675-Chloro-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
120 °C

Procedure

1320 mg (4.7 mmol) of 7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidin-5-ol (Example 138A) are introduced into phosphoryl chloride (20 ml), 3.20 g (14 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 4 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. 1300 mg (92% of theory) of the crude 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

Sources & evidence

ORD record
ord-676474bb8adf4e64838946dd6f7d066f
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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