Toluene → Tert-butyl 2-methyl-4-(2-oxo-1,3,4-oxathiazol-5-yl)benzoate

HRID 1522768Notes

Reaction equation

[C:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:6]([CH3:17])[CH:5]=1)(=[O:3])[NH2:2].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:32]([S:34]Cl)=[O:33]>O1CCOCC1>[CH3:17][C:6]1[CH:5]=[C:4]([C:1]2[O:3][C:32](=[O:33])[S:34][N:2]=2)[CH:16]=[CH:15][C:7]=1[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirring solution of tert-butyl 4-carbamoyl-2-methyl-benzoate (10 g) in mixture of Toluene and Dioxane (3:1, 240 mL) was added potassium carbonate (5.88 g) then chlorocarbonylsulfenyl chloride (5.5 mL). The mixture was heated at 100° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give tert-butyl 2-methyl-4-(2-oxo-1,3,4-oxathiazol-5-yl)benzoate (11.12 g) as a solid. 1H-NMR (CDCl3, 400 MHz): δ=7.87-7.96 (m, 1 H), 7.79-7.87 (m, 2 H), 2.63 (s, 3 H), 1.56-1.64 ppm (m, 9 H).

Workup

temperatureto cool to room temperature
filtrationfiltered
customthe filtrate was evaporated under vacuo
customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-145e7495badf40d68daf92e3aa7de1b9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09078444B2

Reaction notes

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