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Potassium Iodide → 1-(6-Chlorobenzotriazol-1-yl)-propan-2-one

HRID 7216
Notes
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Reaction equation

HRID 7216 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.Cl[CH2:12][C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]([CH2:12][C:13](=[O:15])[CH3:14])[N:7]=[N:8][C:4]=2[CH:3]=1.[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[N:7][N:8]([CH2:12][C:13](=[O:15])[CH3:14])[C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 178418767HCID 178418767, compound

Product 2

HCID 220202521-(6-Chlorobenzotriazol-1-yl)-propan-2-oneHCID 220202531-(5-Chlorobenzotriazol-1-yl)-propan-2-one

Reagents, catalysts & solvents

1
HCID 180AcetoneSolvent

Procedure

A mixture of 5 g of 5-chlorobenzotriazole, 1.4 g of chloroacetone, 5.1 g of potassium carbonate and 0.5 g of potassium iodide is stirred into 50 ml of acetone at room temperature for 48 h. The mixture is subsequently filtered, the filtrate concentrated by evaporation in a vacuum, and the residue purified by flash chromatography. In this way, two isomeric products, 1-(5-chlorobenzotriazol-1-yl)-propan-2-one and 1-(6-chlorobenzotriazol-1-yl)-propan-2-one, are isolated in approximately the same quantities, the first of which is then used directly in the next step.

Workup

  1. filtrationThe mixture is subsequently filtered
  2. concentrationthe filtrate concentrated by evaporation in a vacuum
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-1afeb603539e4cb68b366cc59118d27f
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084280B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes