Sodium Iodide → 5-(2-methyloxiran-2-ylmethylthio)-1-phenyl-1H-tetrazole

HRID 856134Notes

Reaction equation

[C:1]1([N:7]2[C:11]([SH:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O[CH2:23][C:24]2([CH3:27])[CH2:26][O:25]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[CH3:23][C:24]1([CH2:27][S:12][C:11]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[N:9][N:10]=2)[CH2:26][O:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-phenyl-5-mercapto-1H-tetrazole (3.5 g, 19.64 mmol), (2-methyl-2-oxiranylmethyl) toluene-4-sulfonate (5 g, 20.64 mmol), potassium carbonate (3 g, 21.71 mmol), and sodium iodide (4.5 g, 30.02 mmol) in DMF (30 ml) was stirred at 60° C. for 6 hours. The reaction mixture was was poured into water, and extracted with ethyl acetate twice. The extracts were combined, washed with 5% sodium hydroxide aqueous solution and then with water three times, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to afford 5-(2-methyl-2-oxiranylmethylsulfanyl)-1-phenyl-1H-tetrazole (1.9 g, yield 39%) as a colorless oil.

Workup

extractionextracted with ethyl acetate twice
washwashed with 5% sodium hydroxide aqueous solution
dry with materialwith water three times, and dried over sodium sulfate
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-2a3832d3910c437199b83a667faa9980
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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