1H-1,2,4-Triazole → 3,5-Diethoxy-4-[1,2,4]triazol-1-yl-benzaldehyde

HRID 1990887Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH2:14][CH3:15])[C:11]=1F)[CH:7]=[O:8])[CH3:2].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH2:14][CH3:15])[C:11]=1[N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH:7]=[O:8])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3,5-diethoxy-4-fluoro-benzaldehyde (5.00 g, 23.56 mmol, 1.0 equiv; intermediate 21) in DMSO (50 mL) was added 1H-[1,2,4]triazole (3.26 g, 47.12 mmol, 2.0 equiv) and K2CO3 (6.51 g, 47.12 mmol, 2.0 equiv) and the reaction mixture stirred at 110° C. for 1 h. The solution was poured on crashed ice, the reaction mixture extracted with ethyl acetate (2×50 mL) and the combined organic phases dried over MgSO4. The organic solvent was evaporated under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (1:1→0:1) providing 5.28 g (86%) of the title compound. MS (ESI): 261.9 [M+H]+.

Workup

additionThe solution was poured
extractionthe reaction mixture extracted with ethyl acetate (2×50 mL)
dry with materialthe combined organic phases dried over MgSO4
customThe organic solvent was evaporated under reduced pressure
customthe crude reaction product
custompurified with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (1:1→0:1)

Sources & evidence

ORD record: ord-0e1ce44d75d14beeacfb450be94b425e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Reaction notes

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