Potassium Iodide → 4-{2-[(E)-2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzene-sulfonamide

HRID 1768077Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11]CCN2C=CN=N2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:28]=[C:29]([CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([F:45])([F:44])([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:43][S:40]([F:41])([F:42])([F:44])([F:45])[C:37]1[CH:38]=[CH:39][C:34](/[CH:33]=[CH:32]/[C:29]2[O:30][CH:31]=[C:27]([CH2:26][O:1][C:2]3[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:6][CH:7]=3)[N:28]=2)=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 145 mg (0.54 mmol) 4-hydroxy-N-(2-[1,2,3]triazol-1-yl-ethyl)-benzenesulfon-amide and 117 mg (0.36 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 207 mg (0.6 mmol) 4-chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole and 100 mg (0.6 mmol) potassium iodide were added and stirring at 60° C. continued overnight. After evaporation, the residue was mixed with 15 ml water and extracted thrice with 15 ml ethyl acetate. The combined extracts were dried, evaporated and the product purified on silica. Elution with heptane/ethyl acetate 1:5 yielded 148 mg (43%) N-(2-[1,2,3]triazol-1-yl-ethyl)-(4-{2-[(E)-2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzene-sulfonamide as white solid melting at 170–172° C.

Workup

stirringstirring at 60° C.
waitcontinued overnight
customAfter evaporation
additionthe residue was mixed with 15 ml water
extractionextracted thrice with 15 ml ethyl acetate
customThe combined extracts were dried
customevaporated
customthe product purified on silica
washElution with heptane/ethyl acetate 1:5

Sources & evidence

ORD record: ord-221ef2e6085a41aea2a8acff18df47ea
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235574B2

Reaction notes

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