Formaldehyde → (4-ethyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)methanol

HRID 639794Notes

Reaction equation

HRID 639794 reaction equation
[CH2:1]([N:3]1[CH:7]=[N:6][N:5]=[C:4]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:2].[CH2:14]=[O:15]>ClCCl>[NH3:3].[CH2:1]([N:3]1[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:5][N:6]=[C:7]1[CH2:14][OH:15])[CH3:2]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 544930004-(4-Ethyl-4H-[1,2,4]triazol-3-yl)-pyridine

Product 2

HCID 222AmmoniaYield 10%HCID 68431190(4-ethyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-ethyl-4H-[1,2,4]triazol-3-yl)-pyridine (2.55 g, 14.6 mmol) in 37% formaldehyde (˜12 mL) was stirred at 37° C. for 16 hours. Flash chromatography (10% methanolic ammonia in dichloromethane) yielded title product (2.55 g, 85%, used without further purification to remove remaining para-formaldehyde). 1H NMR (CDCl3) δ (ppm): 8.81 (d, 2H), 7.72 (d, 2H), 5.74 (t, 1H), 4.73 (d, 2H), 4.26 (q, 2H), 1.27 (t, 3H).

Sources & evidence

ORD record
ord-7af8350c88ec4759ae5c597cfd684d5a
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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