Potassium Iodide → 3-[{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline

HRID 1258603Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[N:7]([CH3:9])[CH3:8].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Br:27][C:28]1[S:29][CH:30]=[C:31]([CH2:33]Br)[N:32]=1>C(#N)C>[Br:27][C:28]1[S:29][CH:30]=[C:31]([CH2:33][O:1][N:2]=[C:3]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][N:14]=2)[C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:9])[CH3:8])[N:32]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 3-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline (1.25 g, 5.07 mmol) in acetonitrile (50 mL), were added cesium carbonate (3.47 g, 10.6 mmol), potassium iodide (421 mg, 2.53 mmol) and 2-bromo-4-bromomethyl-thiazole (1.44 g, 5.58 mmol). The resulting suspension was stirred at 25° C. for 4 h and 30 minutes. After cooling, the suspension was filtered, the filtrate was diluted with ethyl acetate (250 mL), washed with water (2×100 mL), dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded 3-[{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline as an oil [1.83 g, yield 86%;

Workup

temperatureAfter cooling
filtrationthe suspension was filtered
additionthe filtrate was diluted with ethyl acetate (250 mL)
washwashed with water (2×100 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification on silica gel

Sources & evidence

ORD record: ord-7179a7b0d7b445b19fa1cd3d401bff61
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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