Potassium Iodide → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

HRID 1258595Notes

Reaction equation

HRID 1258595 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][CH3:17])[CH:11]=1)[C:4]1[N:8]([CH3:9])[N:7]=[N:6][N:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Br:26][C:27]1[S:28][CH:29]=[C:30]([CH2:32]Br)[N:31]=1>C(#N)C>[Br:26][C:27]1[S:28][CH:29]=[C:30]([CH2:32][O:1][N:2]=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16][CH3:17])[CH:11]=2)[C:4]2[N:8]([CH3:9])[N:7]=[N:6][N:5]=2)[N:31]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 533022182-Bromo-4-(bromomethyl)-1,3-thiazoleHCID 136352704N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

Product 1

HCID 86653147N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimineYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (1.00 g, 3.73 mmol) in acetonitrile (60 mL), were added cesium carbonate (2.55 g, 7.83 mmol), potassium iodide (310 mg, 1.86 mmol) and 2-bromo-4-bromomethyl-thiazole (1.05 g, 4.10 mmol). The resulting suspension was stirred at 25° C. for 6 h. The suspension was filtered, the solids washed with ethyl acetate and dichloromethane and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), washed with water, dried over MgSO4 concentrated in vacuo. Purification on silica gel afforded N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as an oil that solidified on standing after 2 days [1.49 g, yield 94%; HPLC/MS: m/z=425 (M+H); logP(HCOOH)=3.55].

Workup

  1. filtrationThe suspension was filtered
  2. washthe solids washed with ethyl acetate and dichloromethane
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification on silica gel

Sources & evidence

ORD record
ord-873ede488f7647f9a741175586b90f1d
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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