Potassium Iodide → HCID 69292511, compound

HRID 750984Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH:31]=[CH:32][C:33]2[CH:38]=[CH:37][C:36]([S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40])=[CH:35][CH:34]=2)[O:29][CH:30]=1.[I-].[K+]>CC(=O)CC>[CH3:1][C:2]1[CH:3]=[C:4]([O:17][CH2:25][C:26]2[N:27]=[C:28]([CH:31]=[CH:32][C:33]3[CH:34]=[CH:35][C:36]([S:39]([C:42]([F:45])([F:43])[F:44])(=[O:41])=[O:40])=[CH:37][CH:38]=3)[O:29][CH:30]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[N:13]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 132 mg (0.57 mmol) 3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenol and 186 mg (0.57 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 200 mg (0.57 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfonyl-phenyl)-vinyl]-oxazole and 95 mg (0.57 mmol) potassium iodide were added and stirring at 60° C. continued over night. After evaporation, 50 ml water was added and the mixture extracted with two portions of 50 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated. Chromatography on silica, eluent ethyl acetate, returned 150 mg (49%) pure title compound as light yellow crystals melting at 140-142° C.

Workup

stirringstirring at 60° C.
waitcontinued over night
customAfter evaporation, 50 ml water
additionwas added
extractionthe mixture extracted with two portions of 50 ml ethyl acetate
washThe combined organic layers were washed with 1N sodium hydroxide and water
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-a3f870ba2a6d4327913d617a33fb073d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405231B2

Reaction notes

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