Formaldehyde → N-(1-benzotriazolylmethyl)-2,5-dimethylaniline

HRID 743154Notes

Reaction equation

HRID 743154 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[N:11]1.[CH2:19]=O>CCO>[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH2:19][NH:4][C:3]3[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:2]=3[CH3:1])[C:13]=2[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 72592,5-DimethylanilineHCID 178418385HCID 178418385, compound

Product 1

HCID 178425127N-(1-benzotriazolylmethyl)-2,5-dimethylanilineYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,5-dimethylaniline (27.4 g, 0.2 mol) and benzotriazole (23.8 g, 0.2 mol) in EtOH (300 mL) was stirred at 20° C. as 37% aqueous formaldehyde (16.1 g, 0.2 mol) was added gradually. After 30 minutes, the white solid which precipitated was collected and washed with EtOH to give N-(1-benzotriazolylmethyl)-2,5-dimethylaniline (33.9 g, 67% yield); mp (EtOH) 147°-149° C.

Workup

  1. additionwas added gradually
  2. customthe white solid which precipitated
  3. customwas collected
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-f57de443db82430f9b8339c8eac2cbf0
Source dataset
uspto-grants-1996_09
Patent number
US05556874

Reaction notes

Loading…