Water → 4-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2239536Notes

Reaction equation

CN(C=O)C.[C:6]([Cl:11])(=O)[C:7](Cl)=[O:8].OC1C(=O)[N:15]([CH:26]([CH3:28])[CH3:27])[S:16](=[O:25])(=[O:24])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[Cl:11][C:6]1[C:7](=[O:8])[N:15]([CH:26]([CH3:28])[CH3:27])[S:16](=[O:24])(=[O:25])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

DMF (25 mL) and oxalyl chloride (0.2 mL, 2.29 mmol) were added separately to a solution of 4-hydroxy-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.5 g, 1.87 mmol) in DCM (25 mL) at 0° C. The reaction mixture was then heated at 50° C. for 4 h, water was added and the resulting mixture was extracted with EtOAc. The combined organic layers were washed with water, then brine and evaporated. The residue was purified by silica gel column chromatography using a 4:1 mixture of hexane and EtOAc as eluant to give the title compound (0.25 g, 46%) as a solid; 1H NMR (200 MHz, CDCl3): δ 8.10-7.94 (m, 2H), 7.61-7.50 (m, 3H), 4.50 (sep, 1H), 1.61 (s, 3H), 1.65 (s, 6H).

Workup

extractionthe resulting mixture was extracted with EtOAc
washThe combined organic layers were washed with water
custombrine and evaporated
customThe residue was purified by silica gel column chromatography
additiona 4:1 mixture of hexane and EtOAc as eluant

Sources & evidence

ORD record: ord-2d00769d529e4206921f32a216d183ab
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723333B2

Reaction notes

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