Formaldehyde → (dimethyl-4H-1,2,4-triazol-3-yl)methanol

HRID 907916Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][N:3]=1.[CH2:8]=[O:9]>>[CH3:7][N:6]1[C:2]([CH3:1])=[N:3][N:4]=[C:5]1[CH2:8][OH:9]

Participants

Reactant 2

HCID 712Formaldehyde

HCID 122170533,4-dimethyl-4H-1,2,4-triazole

Product 1

HCID 18726738(dimethyl-4H-1,2,4-triazol-3-yl)methanolYield 82%

Conditions

Temperature: 90 °C

Procedure

A mixture of 3,4-dimethyl-4H-1,2,4-triazole (2.3 g, 23.7 mmol) and formalin (5 mL) was heated to 90° C. overnight. The mixture was concentrated to give crude product. The crude product was purified by silica gel chromatography (dichloromethane/methanol=200:1 to 15:1) to give the title compound (2.48 g, yield 82%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.31 (s, 3H), 3.52 (s, 3H), 4.52-4.54 (d, J=5.2 Hz, 2H), 5.49-5.51 (t, J=5.2 Hz, 1H). LC-MS (ESI) m/z: 128 (M+1)+.

Workup

concentrationThe mixture was concentrated
customto give crude product
customThe crude product was purified by silica gel chromatography (dichloromethane/methanol=200:1 to 15:1)

Sources & evidence

ORD record: ord-9279f2ec5d9c4ce3a6b0b4e6b0f2d970
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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