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

HRID 273897

Reaction equation

HRID 273897 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C=O.[C:25]1(C)C=CC=CC=1>C(O)CCC>[OH:1][C:2]1[C:7]([CH2:25][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 8021DiethylamineHCID 17113Drometrizole

Product 1

HCID 159190222-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-(2-Hydroxy-5-methylphenyl)-2H-benzotriazole (74.3 g, 0.33 tool), diethylamine (37.0 g, 0.51 mol) and paraformaldehyde (17.1 g) are dissolved in 85 mL of n-butanol. The mixture is heated with agitation at reflux (95° to 100° C.) for 44 hours. The solvent is then removed by vacuum distillation to give a yellow viscous liquid 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. temperatureat reflux (95° to 100° C.) for 44 hours
  3. customThe solvent is then removed by vacuum distillation
  4. customto give a yellow viscous liquid as product
  5. customin high yield (>99%)

Sources & evidence

ORD record
ord-50be053378cd4aac916212eea72f6f37
Source dataset
uspto-grants-1995_02
Patent number
US05387691

Linked notes

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