Iodine → HCID 23368336, compound

HRID 1901549Notes

Reaction equation

HRID 1901549 reaction equation
[CH3:1][O:2][C:3]1[C:7]([C:8]#[N:9])=[C:6](S(C)(=O)=O)[S:5][N:4]=1.[CH2:14]([OH:18])[CH2:15][C:16]#[CH:17].[OH-].[K+].[I:21]I.[I-].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([O:18][CH2:14][CH2:15][C:16]#[C:17][I:21])[S:5][N:4]=1

Participants

8

Reactant 5

HCID 807IodineHCID 4875Potassium IodideHCID 135663-Butyn-1-OLHCID 14797Potassium Hydroxide2×HCID 612668HCID 612668, compound

Product 1

HCID 23368336HCID 23368336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.2 Grams of 3-methoxy-4-cyano-5-methylsulfonylisothiazole was dissolved in 20 ml of DMF, and 1.5 g of 3-butyn-1-ol and 4.3 g of 30% KOH were added at room temperature with stirring, after which the reaction solution was stirred for 2 hours. The reaction solution was ice-cooled to 5° to 10° C., 5.1 g of iodine and 3.2 g of potassium iodide were added thereto with stirring, and then 6.6 g of 10% KOH was added dropwise. The temperature of the reaction solution was returned to room temperature, and after stirring 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. The crystals were recrystallized from ether to obtain 2.1 g of crystals having a melting point of 71° to 73° C.

Workup

  1. stirringafter which the reaction solution was stirred for 2 hours
  2. temperaturecooled to 5° to 10° C.
  3. stirringwith stirring
  4. customwas returned to room temperature
  5. stirringafter stirring for 1 hour
  6. extractionwas then extracted with ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customto obtain crude crystals
  11. customThe crystals were recrystallized from ether

Sources & evidence

ORD record
ord-6919478c4a2e42578130c083ff8bd794
Source dataset
uspto-grants-1996_11
Patent number
US05578622

Reaction notes

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