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

HRID 729265Notes

Reaction equation

HRID 729265 reaction equation
CN(C=O)C.[C:6]([Cl:11])(=O)[C:7](Cl)=[O:8].OC1C(=O)[NH:15][S:16](=[O:25])(=[O:24])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:11][C:6]1[C:7](=[O:8])[NH:15][S:16](=[O:24])(=[O:25])[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6855393(2H)-Isothiazolone, 4-hydroxy-5-phenyl-, 1,1-dioxide

Product 1

HCID 686616564-Chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry DMF (1.2 ml) was added dropwise to a mixture of oxalyl chloride (4.96 g, 39.1 mmol) and 4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide (2.2 g, 9.77 mmol) in DCM. The resulting solution was heated under reflux until it turned orange. The mixture was then cooled to room temperature and filtered affording the title compound (1.18 g, 50%) as white solid. 1H NMR (400 MHz, d6-DMSO): δ 7.41-7.54 (m, 3H), 7.77-7.80 (m, 2H), 12.70 (br.s, 1H); 13C-NMR (100 MHz, d6-DMSO): δ 126.1, 127.1, 128.3, 129.9, 130.6, 144.9, 162.2.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux until it
  3. filtrationfiltered

Sources & evidence

ORD record
ord-27d9d5d1431b42cd9f91b9fe91de0773
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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