Water → HCID 86629255, compound

HRID 424842Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.[Cl:19][C:20]1[CH:27]=[C:26](F)[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:19][C:20]1[CH:27]=[C:26]([O:15][CH2:14][C:13]2[N:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[N:11][C:12]=2[CH:16]([CH3:18])[CH3:17])[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]

Participants

Conditions

Temperature: 100 °C

Procedure

To solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (0.100 g, 1 eq) and 2-chloro-4-fluorobenzaldehyde (0.11 g, 2 eq) in dimethylformamide (3 mL) is added cesium carbonate (0.23 g, 2 eq). The reaction is heated to 100° C. overnight. The reaction is cooled to room temperature and water is added. The mixture is extracted with ethyl acetate and the organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with 0-10% ethyl acetate:toluene to give 0.101 g of 2-Chloro-4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-benzaldehyde. ES/MS m/e 426.1 (M+1).

Workup

temperatureThe reaction is cooled to room temperature
extractionThe mixture is extracted with ethyl acetate
washthe organic layers are washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified via flash chromatography
washeluting with 0-10% ethyl acetate

Sources & evidence

ORD record: ord-544091557a954a169c99ba429ed77bf9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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