Formaldehyde → HCID 70011202, compound

HRID 1276857Notes

Reaction equation

HRID 1276857 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-aa90713cc525452c9cf4cbe5912ece67
Source dataset
uspto-grants-2000_12
Patent number
US06166218

Reaction notes

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