Water → HCID 19806678, compound
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
[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]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.
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