Cyanuric chloride → (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)amine

HRID 563847Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]1[C:14]([Cl:15])=[N:13][C:11](Cl)=[N:10][C:8]=1[Cl:9].[F:16][C:17]([F:27])([F:26])[C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[F:25])[NH2:21]>C1COCC1.O>[Cl:15][C:14]1[N:7]=[C:8]([Cl:9])[N:10]=[C:11]([NH:21][C:20]2[CH:22]=[CH:23][C:24]([F:25])=[C:18]([C:17]([F:27])([F:16])[F:26])[CH:19]=2)[N:13]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

Potassium carbonate (2.76 g, 20 mmol) was added to a solution of cyanuric chloride (II) (1.84 g, 10 mmol) in THF (30 mL) and the mixture cooled to 0-5° C. in an ice bath. 3-Trifluoromethyl-4-fluoroaniline (XVI) (1.79 g, 10 mmol) was added dropwise with stirring. The mixture was stirred for 16 h, diluted with water (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extract was rinsed with brine (20 mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified by chromatography (silica gel; EtOAc/hexane (1:4)) to afford 4,6-dichloro-N-(3-trifluoromethyl-4-fluorophenyl)-1,3,5-triazine-2-amine (XVII) as an off-white solid (0.9 g, 19% yield): m.p. 114-117° C.; 1H NMR (CDCl3) δ 7.80 (s, 1H), 7.86 (m, 2H), 7.65 (bs, 1H), 7.27 (t, 1H); ESI/MS 326 (M+H).

Workup

stirringThe mixture was stirred for 16 h
extractionextracted with ethyl acetate (3×20 mL)
extractionThe combined organic extract
washwas rinsed with brine (20 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by chromatography (silica gel; EtOAc/hexane (1:4))

Sources & evidence

ORD record: ord-6f7846c5bcd8464ba51c2f1e9c9b2b28
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067588B2

Reaction notes

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