1H-Benzotriazole-1-methanol → N-{1-(1H-Benzotriazolyl)methyl}-4-benzyloxy-2-fluoroaniline

HRID 388021Notes

Reaction equation

HRID 388021 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]1([CH2:26]O)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1>CO>[N:17]1([CH2:26][NH:13][C:12]2[CH:14]=[CH:15][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[F:16])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

Participants

4

Reactant 2

HCID 2241691H-Benzotriazole-1-methanolHCID 114998094-(Benzyloxy)-2-fluoroaniline

Product 1

HCID 22936313N-{1-(1H-Benzotriazolyl)methyl}-4-benzyloxy-2-fluoroanilineYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dissolving 4-benzyloxy-2-fluoroaniline (11.25 g, 51.78 mmol) in methanol (300 ml), 1H-benzotriazole-1-methanol (8.11 g, 54.37 mmol) was added and the mixture was stirred for 10 hours at room temperature. The precipitated crystals were filtered out, washed with ethanol and dried by aspiration to obtain the title compound (12.01 g, 34.47 mmol, 66.57%) as colorless crystals.

Workup

  1. additionwas added
  2. filtrationThe precipitated crystals were filtered out
  3. washwashed with ethanol
  4. customdried by aspiration

Sources & evidence

ORD record
ord-cc5446e4087a46568ebdea5815b005e6
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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