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

HRID 729264Notes

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-e4724bc21ba04a22910d0e27156dbaca
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582629B2

Reaction notes

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