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

HRID 1033795Notes

Reaction equation

HRID 1033795 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

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 removed by a vacuum distillation, and the product, an off-white solid, is obtained in high yield (>99%). This Mannich base is identified by thin layer chromatography using toluene as the mobile phase.

Workup

  1. temperatureThe mixture is heated with agitation
  2. temperatureat reflux (95° to 100° C.) for 50 hours
  3. customThe solvent is removed by a vacuum distillation
  4. customthe product, an off-white solid, is obtained
  5. customin high yield (>99%)

Sources & evidence

ORD record
ord-a6af51c40e01429d9112a5bddb9c5fd8
Source dataset
uspto-grants-1994_05
Patent number
US05312852

Reaction notes

Loading…