Potassium Iodide → HCID 10665070, compound

HRID 1633528Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[CH:18]=[C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]4=[CH:15][C:14]=3[NH:13][C:12]=2[CH:11]=[C:10]([OH:27])[CH:9]=1.[I-].[K+].Cl[C:31]([CH3:35])([CH3:34])[C:32]#[CH:33]>CN(C)C=O>[OH:7][C:8]1[CH:9]=[C:10]2[O:27][C:31]([CH3:35])([CH3:34])[CH:32]=[CH:33][C:11]2=[C:12]2[C:21]=1[C:20](=[O:22])[C:19]1[CH:18]=[C:17]3[CH:23]=[CH:24][CH:25]=[CH:26][C:16]3=[CH:15][C:14]=1[NH:13]2

Participants

Conditions

Temperature: 65 °C

Procedure

2 g of anhydrous potassium carbonate are added, under an inert atmosphere, to a solution of 2 g of the product of Step A in 50 ml of anhydrous dimethylformamide. After stirring for 15 minutes at 65° C., 2.4 g of anhydrous potassium iodide and 4.4 g of 3-chloro-3-methyl-1-butyne are added and the reaction mixture is maintained at 65° C. for 24 hours and then at 130° C. for 1 hour 30 minutes. After cooling, the solution is hydrolysed and then extracted with dichloromethane. The combined organic phases are washed with water and then with a 1M potassium hydroxide solution, dried over sodium sulphate and then evaporated. Chromatography over silica gel (cyclohexane/acetone: 90/10) yields 1.10 g of the expected product.

Workup

temperaturethe reaction mixture is maintained at 65° C. for 24 hours
waitat 130° C. for 1 hour 30 minutes
temperatureAfter cooling
extractionextracted with dichloromethane
washThe combined organic phases are washed with water
dry with materialwith a 1M potassium hydroxide solution, dried over sodium sulphate
customevaporated

Sources & evidence

ORD record: ord-5540d1cb7ab24cc1bb7bd454490be6d1
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503919B1

Reaction notes

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