Phosphorus oxychloride → HCID 59313005, compound

HRID 2389816Notes

Reaction equation

HRID 2389816 reaction equation
O[C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[N:3]=1.P(Cl)(Cl)([Cl:28])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:28][C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[N:3]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470152HCID 178470152, compound

Product 1

HCID 59313005HCID 59313005, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
120 °C

Procedure

2300 mg (6.5 mmol) of ethyl 5-hydroxy-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo-[1,5-c]pyrimidine-2-carboxylate (Example 133A) are introduced into phosphoryl chloride (30 ml), 5.95 g (26.1 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 20 h. The reaction mixture is slowly poured, while stirring vigorously, into saturated sodium bicarbonate solution (200 ml) and ice, and solid sodium bicarbonate (approx. 20 g) is added until a pH of 8 is reached. The solid is filtered off with suction and washed with water and diethyl ether and dried. 2300 mg (92% 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. washwashed with water and diethyl ether
  6. customdried
  7. custom2300 mg (92% of theory) of the product are obtained

Sources & evidence

ORD record
ord-6278ac842da0478eb7ae98ac176eca8e
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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