Iodine → HCID 23368328, compound

HRID 1901544Notes

Reaction equation

HRID 1901544 reaction equation
[OH:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]#[CH:19].[I:21]I.[I-].[K+].[OH-].[K+]>CN(C=O)C.O>[I:21][C:19]#[C:18][CH2:17][O:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1

Participants

9

Reactant 6

HCID 807IodineHCID 4875Potassium IodideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178503646HCID 178503646, compound

Product 1

HCID 23368328HCID 23368328, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.72 Grams of 3-hydroxy-4-cyano-5-methylthioisothiazole was dissolved in 20 ml of DMF, 0.7 g of potassium carbonate was added thereto, and then 1.3 g of propargyl bromide was added with stirring. After stirring at 50° C. for 1 hour, the reaction solution was ice-cooled, 3.0 g of iodine and 3.2 g of potassium iodide were added thereto, and then 6.6 g of a 10% KOH was gradually added dropwise with stirring. After addition, the reaction solution was stirred at room temperature for 1 hour. Water was added to the reaction solution to precipitate crystals, which were then collected by filtration and washed with water to obtain crude crystals. Recrystallization of the crude crystals from ether gave 2.5 g of crystals having a melting point of 145° to 146° C. (yield, 75%).

Workup

  1. stirringAfter stirring at 50° C. for 1 hour
  2. temperaturecooled
  3. stirringwith stirring
  4. additionAfter addition
  5. stirringthe reaction solution was stirred at room temperature for 1 hour
  6. customto precipitate crystals, which
  7. filtrationwere then collected by filtration
  8. washwashed with water
  9. customto obtain crude crystals
  10. customRecrystallization of the crude crystals from ether

Sources & evidence

ORD record
ord-46fd10bd821846899a7fc54a253a47c7
Source dataset
uspto-grants-1996_11
Patent number
US05578622

Reaction notes

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