Potassium Iodide → 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide

HRID 1042337Notes

Reaction equation

HRID 1042337 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:17]([C:19]1[N:24]=[C:23]([NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=[CH:21][CH:20]=1)[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C1OCCOC1>[CH3:28][C:27]([CH3:29])([CH3:30])[C:26]([NH:25][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:17]([O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:18])[N:24]=1)=[O:31]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 66860075N-[6-(1-bromoethyl)pyridin-2-yl]-2,2-dimethylpropanamideHCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 866499712,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (10 g, 49.21 mmol, 1 eq.) in 250 ml of dioxanne, was added N-[6-(1-bromoethyl)pyridin-2-yl]-2,2-dimethylpropanamide (14 g, 49.21 mmol, 1 eq.), then was added cesium carbonate (16 g, 49.21 mmol, 1 eq.), and then was added potassium iodide (0.81 g, 4.92 mmol, 0.1 eq.). The reaction mixture was stirred for further 36 hrs. After evaporation of the solvent, the white residue was taken up with 200 ml of water, triturated and filtered, yielding to 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide (19.7 g, 90% pure, 88% yield) after air-drying.

Workup

  1. customAfter evaporation of the solvent
  2. customtriturated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9bf32ea6cba94c38aaa94b9be83fcc5c
Source dataset
uspto-grants-2013_10
Patent number
US08557849B2

Reaction notes

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