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Potassium Iodide → HCID 10665070, compound

HRID 478683
Notes
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Reaction equation

HRID 478683 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[C:31]([CH3:35])([CH3:34])[C:32]#[CH:33]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]2[O:21][C:31]([CH3:35])([CH3:34])[CH:32]=[CH:33][C:5]2=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[C:11]3[CH:17]=[CH:18][CH:19]=[CH:20][C:10]3=[CH:9][C:8]=1[NH:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 706791-Butyne, 3-chloro-3-methyl-HCID 10540475HCID 10540475, compound

Product 1

HCID 10665070HCID 10665070, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2 g of the product of Step A in 50 ml of anhydrous dimethylformamide, under an inert atmosphere, there are added 2 g of anhydrous potassium carbonate. 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 held at 65° C. for 24 hours and then at 130° C. for 1 hour. After cooling, the solution is hydrolysed and then extracted with dichloromethane. The combined organic phases are washed with water and then with 1M potassium hydroxide solution, dried over sodium sulphate and then evaporated. After chromatography over silica gel (cyclohexane/acetone: 90/10), 1.10 g of the expected product are isolated.

Workup

  1. waitthe reaction mixture is held at 65° C. for 24 hours
  2. waitat 130° C. for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases are washed with water
  6. dry with materialwith 1M potassium hydroxide solution, dried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-7b139e78e28c40b5a6266bd06556f2b7
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642248B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes