18-Crown-6 → HCID 19847866, compound

HRID 2350933Notes

Reaction equation

Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])[N:5]=[C:4]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[N:3]=1.[F-:25].[K+].C1OCCOCCOCCOCCOCCOC1>S1(CCCC1)(=O)=O>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[C:4]1[N:3]=[C:2]([F:25])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])[N:5]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2.61 g (6.9 mmol) of 5-chloro-3-(2-chloro-6-fluorophenyl)-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole, 0.84 g (14.5 mmol) of dry potassium fluoride and 0.23 g (0.9 mmol) of 18-crown-6 in 15 ml of dry sulfolane is heated at 140° C. for 65 hours. The reaction mixture is subsequently cooled and eluted on silica gel (φ 40-63 μm, column: 0 7 cm, height 20 cm) with ethyl acetate/n-hexane (7:13). There is obtained 3-(2-chloro-6-fluorophenyl)-5-fluoro-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole as white crystals, m.p. 68°-70° C.; mass spectrum: 359(100).

Workup

temperatureThe reaction mixture is subsequently cooled
washeluted on silica gel (φ 40-63 μm, column: 0 7 cm, height 20 cm) with ethyl acetate/n-hexane (7:13)

Sources & evidence

ORD record: ord-fdc698787b65495288d3c0874068726f
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871757

Reaction notes

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