Water → HCID 19806678, compound

HRID 1681465Notes

Reaction equation

HRID 1681465 reaction equation
[Cl:1][C:2]1[C:3]([OH:8])=[N:4][S:5][C:6]=1[Cl:7].C(=O)([O-])[O-].[K+].[K+].[CH2:15](I)[CH3:16].O>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:8][CH2:15][CH3:16])=[N:4][S:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178519014HCID 178519014, compound

Product 1

HCID 19806678HCID 19806678, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 4,5-dichloro-3-hydroxyisothiazole (17.00 g, 0.100 mol) and potassium carbonate (13.82 g, 0.100 mol) in dry DMF (80 ml) was added dropwise a solution of ethyl iodide (8.84 ml, 0.110 mol) in dry DMF (20 ml). The mixture was stirred 18 hours at ambient temperature. Water (500 ml) was added and the mixture was extracted with ether (3×400 ml). The combined ether extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product (18.35 g). The crude product was distilled to give 4,5-dichloro-3-ethoxyisothiazole (14.63 g, 74%, b.p. 64°-66°/0.1 mm). TLC (2% methanol/chloroform, silica): Rf=0.72.

Workup

  1. extractionthe mixture was extracted with ether (3×400 ml)
  2. dry with materialThe combined ether extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude product (18.35 g)
  6. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-67a87734d60e4d9b8b953ad89a1cfece
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

Loading…