Formaldehyde → HCID 4352105, compound

HRID 570560Notes

Reaction equation

HRID 570560 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH3:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]=O>CO.C(OCC)C>[N:1]1([CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:19])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7669N-MethylbenzylamineHCID 178418385HCID 178418385, compound

Product 1

HCID 4352105HCID 4352105, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Benzotriazole (6 g, 50 mmol) and N-methylbenzylamine (10.57 ml, 55 mmol) were dissolved in methanol (MeOH) (25 ml) followed by drop wise addition of formaldehyde (4.9 ml, 37% in H2O). The resulting mixture was heated at 50° C. for 15 h and cooled to ambient temperature. It was then diluted with diethyl ether (Et2O) (100 ml), washed with saturated sodium chloride aqueous solution (brine) (2×70 ml) and dried over magnesium sulfate (MgSO4) and concentrated. Upon further drying under reduced pressure, the material solidified to afford the depicted compound (13.2 g, 85%).

Workup

  1. temperaturecooled to ambient temperature
  2. washwashed with saturated sodium chloride aqueous solution (brine) (2×70 ml)
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. concentrationconcentrated
  5. customUpon further drying under reduced pressure

Sources & evidence

ORD record
ord-969e959312354db4a71aacb72c1b5383
Source dataset
uspto-grants-2015_05
Patent number
US09023860B2

Reaction notes

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