Formaldehyde → 2-(5-Hydroxymethyl-1,2,4-triazol-1-yl)ethanol

HRID 277332

Reaction equation

HRID 277332 reaction equation
[N:1]1([CH2:6][CH2:7][OH:8])[CH:5]=[N:4][CH:3]=[N:2]1.[CH2:9]=[O:10]>>[OH:10][CH2:9][C:5]1[N:1]([CH2:6][CH2:7][OH:8])[N:2]=[CH:3][N:4]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 5509251H-1,2,4-Triazole-1-ethanol

Product 1

HCID 183145282-(5-Hydroxymethyl-1,2,4-triazol-1-yl)ethanolYield 68%

Conditions

Temperature
135 °C

Procedure

A solution of 2-(1,2,4-triazol-1yl)ethanol (5.0 g, 44 mmol) in 38% w/v aqueous formaldehyde (25 ml) was stirred and heated at 135° C. in a sealed tube for 18 hours. Upon cooling the volatiles were removed in vacuo (azeotroping with ethanol). The residue was purified by chromatography on silica gel, eluting with 5→10→15% methanol-dichloromethane to give the title compound (4.3 g, 68%) as a thick oil. 1H NMR (360 MHz, d6-DMSO) δ 3.69-3.74 (2H, m), 4.24 (2H, t, J=5.7 Hz), 4.60 (2H, d, J=5.7 Hz), 4.96 (1H, t, J=5.3 Hz), 5.51 (1H, t, J=5.8 Hz), 7.84 (1H, s); MS (ES+) m/e 144 [MH]+.

Workup

  1. temperatureUpon cooling the volatiles
  2. customwere removed in vacuo (azeotroping with ethanol)
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with 5→10→15% methanol-dichloromethane

Sources & evidence

ORD record
ord-b27575f832e7405897e6d72dd1866d46
Source dataset
uspto-grants-2002_03
Patent number
US06355798B1

Linked notes

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