Iodine → HCID 23368330, compound

HRID 1901547Notes

Reaction equation

HRID 1901547 reaction equation
[OH:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH2:10][CH3:11])[S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:21][CH2:22]Cl)[C:19]#[CH:20].[I:24]I.[I-].[K+].[OH-].[K+]>CN(C=O)C.O>[I:24][C:20]#[C:19][CH2:18][O:21][CH2:22][O:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH2:10][CH3:11])[S:4][N:3]=1

Participants

9

Reactant 6

HCID 807IodineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 122413411-Propyne, 3-(chloromethoxy)-HCID 178477412HCID 178477412, compound

Product 1

HCID 23368330HCID 23368330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

1.86 Grams of 3-hydroxy-4-cyano-5-ethylthioisothiazole was dissolved in 30 ml of DMF, and 0.7 g of potassium carbonate was added thereto. Thereafter, 1.3 g of 2-propynyloxymethyl chloride was added at room temperature with stirring, and the reaction solution was stirred at 50° C. for 2 hours. The reaction solution was ice-cooled to 5° to 10° C., a solution of 5.0 g of iodine and 3.2 g of potassium iodide in 5 ml of water and 20 ml of DMF was added thereto, and then 6.6 g of 10% KOH was added dropwise. After addition, the reaction solution was stirred at room temperature for 1 hour. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure to obtain crude crystals. Recrystallization of the crude crystals from ether/hexane gave 2.6 g of crystals having a melting point of 57° to 58° C.

Workup

  1. stirringthe reaction solution was stirred at 50° C. for 2 hours
  2. temperaturecooled to 5° to 10° C.
  3. additionAfter addition
  4. stirringthe reaction solution was stirred at room temperature for 1 hour
  5. extractionwas then extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude crystals
  10. customRecrystallization of the crude crystals from ether/hexane

Sources & evidence

ORD record
ord-206ec59a533a485081bcfa7752100355
Source dataset
uspto-grants-1996_11
Patent number
US05578622

Reaction notes

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