Formaldehyde → HCID 70011202, compound

HRID 990204Notes

Reaction equation

HRID 990204 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]=O.[CH2:27]([NH:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>>[OH:1][C:2]1[C:7]([CH2:25][N:31]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:27][CH2:28][CH2:29][CH3:30])=[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

4

Reactant 3

HCID 712FormaldehydeHCID 8148DibutylamineHCID 62485Octrizole

Product 1

HCID 70011202HCID 70011202, compoundYield 96%

Conditions

Temperature
160 °C

Procedure

2-[2-Hydroxy-5-tert-octylphenyl]-2H-benzotriazole (30 g, 0.092 mol), paraformaldehyde (3 g, 0.0955 mol) and di-n-butylamine (24.9 g, 0.191 mol) are charged to a pressure reaction at ambient temperature. The reactor is sealed and the temperature raised to 160° C. The reaction mass is held at 160° C. for four hours and then discharged. The reactor is rinsed with toluene. The toluene, amine and water are stripped by rotary evaporation. The crude product is prepared in a 96% yield (40 g). This product is chromatographed on silica gel using a heptane/ethyl acetate gradient as eluent to remove a trace of unreacted starting benzotriazole intermediate. The title compound is a yellow oil whose structure is confirmed by 1Hnmr.

Workup

  1. customThe reactor is sealed
  2. washThe reactor is rinsed with toluene
  3. customThe toluene, amine and water are stripped by rotary evaporation
  4. customThis product is chromatographed on silica gel using a heptane/ethyl acetate gradient as eluent
  5. customto remove a trace

Sources & evidence

ORD record
ord-7f4360f84ddb4ec8a382867aabe6b584
Source dataset
uspto-grants-2002_10
Patent number
US06458872B1

Reaction notes

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