Iodine → HCID 23368335, compound

HRID 1901551Notes

Reaction equation

[OH:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1.[CH3:11][C:12](Cl)([O:14][CH2:15][C:16]#[CH:17])[CH3:13].[I:19]I.[I-].[K+].[OH-].[K+]>CN(C=O)C>[I:19][C:17]#[C:16][CH2:15][O:14][C:12]([CH3:13])([CH3:11])[O:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.7 Grams of 3-hydroxy-4-cyano-5-methylthioisothiazole was dissolved in 30 ml of DMF, 1.4 g of 1,1-dimethyl-2-propynyloxymethyl chloride was added thereto, and then the reaction solution was stirred at 50° C. for 1 hour. Thereafter, the reaction solution was ice-cooled to 5° to 10° C., 5.1 g of iodine and 3.5 g of potassium iodide were added thereto, 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, the reaction solution was 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 2.4 g of crystals having a melting point of 96° to 97° C. (yield 60%).

Workup

temperaturecooled to 5° to 10° C.
customwas returned to room temperature
stirringafter stirring for 1 hour
extractionthe reaction solution was extracted with ethyl acetate
washThe extract was washed with water
customdried
concentrationconcentrated under reduced pressure
customto obtain crude crystals
customThe crystals were recrystallized from ether

Sources & evidence

ORD record: ord-e40c96a4a7854cac9d0dc14f489e3ecf
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578622

Reaction notes

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