Potassium Carbonate → 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(naphthalen-1-yl)ethanone

HRID 386395Notes

Reaction equation

HRID 386395 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[N:15]1([CH2:2][C:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)=[O:4])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38305132-Bromo-1-(1-naphthalenyl)ethanoneHCID 178418385HCID 178418385, compound

Product 1

HCID 668208062-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(naphthalen-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-1-(naphthalen-1-yl)ethanone (1 g, 4.02 mmol), benzotriazole (530 mg, 4.42 mmol) and K2CO3 (560 mg, 4.02 mmol) in toluene (100 mL) was heated at reflux for 16 hours. The reaction was cooled to room temperature, washed with water, dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (100% DCM) afforded 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(naphthalen-1-yl)ethanone as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by preparative thin layer chromatography (100% DCM)

Sources & evidence

ORD record
ord-289745e35a7e41798d04cf1236963728
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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