m-Chloroperbenzoic acid → HCID 25050367, compound

HRID 1020244Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][O:16][CH2:17][CH2:18][S:19][CH3:20])[N:14]=1)=[O:8].ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][O:16][CH2:17][CH2:18][S:19]([CH3:20])=[O:33])[N:14]=1)=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3,4-Dichlorobenzyl)-3-(4-((2-(methylthio)ethoxy)methyl)thiazol-2-yl)urea (Example 26) (0.98 mmol, 0.4 g) was dissolved in CHCl3 (10 mL) and cooled to 0° C. 3-Chloroperbenzoic acid (1 eq, 0.98 mmol, 0.17 g) was added and the mixture was stirred at room temperature overnight. LC-MS indicated the product was a mixture of sulfoxide and sulfone. Sodium bicarbonate (saturated, 10 mL) was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated to give an oil. Purification by preparative HPLC yielded 0.048 g of the title compound as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.49-7.45 (m, 2H), 7.25 (m, 1H), 6.85 (s, 1H), 4.87 (s, 2H), 4.45 (s, 2H), 3.86 (m, 2H), 3.11-2.91 (m, 2H), 2.65 (s, 3H).

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with CH2Cl2 (2×20 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customto give an oil
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-e93186d491134626a9718039377cbae1
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716320B2

Reaction notes

Loading…