Formaldehyde → 2-(2-Hydroxy-3-diethylaminomethyl-5-tert-octylphenyl)-2H-benzotriazole

HRID 1756467Notes

Reaction equation

HRID 1756467 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[N:17]1.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26].C=O.[C:32]1(C)C=CC=CC=1>C(O)CCC>[OH:1][C:2]1[C:7]([CH2:32][N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:6][C:5]([C:8]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:9])[CH3:10])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[N:17]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 8021DiethylamineHCID 62485Octrizole

Product 1

HCID 152194142-(2-Hydroxy-3-diethylaminomethyl-5-tert-octylphenyl)-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
97.5 °C

Procedure

2-(2-Hydroxy-5-tert-octylphenyl)-2H-benzotriazole (70.0 g, 0.22 mol), diethylamine (24.3 g, 0.33 mol) and paraformaldehyde (11.2 g) are dissolved in 55 mL of n-butanol. The mixture is heated with agitation at reflux (95 to 100° C.) for 50 hours. The solvent is then removed by vacuum distillation to give an off-white solid as product in high yield (>99%). This Mannich base is identified as the above-named compound by thin layer chromatography using toluene as the mobile phase.

Workup

  1. temperatureThe mixture is heated with agitation
  2. customThe solvent is then removed by vacuum distillation
  3. customto give an off-white solid as product
  4. customin high yield (>99%)

Sources & evidence

ORD record
ord-269ef79829ce4dff803167c1da011da4
Source dataset
uspto-grants-1995_08
Patent number
US05439955

Reaction notes

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