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

HRID 2171547Notes

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]([F:22])([F:21])[F:20])[N:18]=[C:11]2[CH:10]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:30])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:30][C:13]1[N:12]2[N:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=[C:11]2[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

950 mg (2.7 mmol) of 7-(2,4-dichlorophenyl)-2-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-ol (Example 130A) are introduced into phosphoryl chloride (10 ml), 1.86 g (8.2 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 12 h. The reaction mixture is slowly poured, with vigorous stirring, into saturated sodium bicarbonate solution and ice, and solid sodium bicarbonate (approx. 5 g) is added until a pH of 8 is reached. The solid is filtered off with suction. The reaction vessel is washed out with dichloromethane, and the organic phase is dried over magnesium sulphate, concentrated and combined with the filtered solid. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1). 784 mg (78% of theory) of the product are obtained.

Workup

additionare added
additionis added until a pH of 8
filtrationThe solid is filtered off with suction
washThe reaction vessel is washed out with dichloromethane
dry with materialthe organic phase is dried over magnesium sulphate
concentrationconcentrated
customThe crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1)
custom784 mg (78% of theory) of the product are obtained

Sources & evidence

ORD record: ord-d312d749a7c14c6ea347c00fd13f7d61
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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