Sulfuric acid magnesium salt (1:1) → HCID 103596197, compound

HRID 709439Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:13][C:14]([S@:17](/[N:19]=[CH:5]/[C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[C:2]([F:12])([F:11])[F:1])=[O:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 40 °C

Procedure

To a 100-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was added CH2Cl2 (50 mL), 2-(trifluoromethyl)benzaldehyde (2.01 g, 11.54 mmol, 1.00 equiv), (R)-(+)-2-methylpropane-2-sulfinamide (1.68 g, 13.86 mmol, 1.20 equiv), pyridinium p-toluenesulfonate (0.145 g, 0.05 equiv) and magnesium sulfate (6.93 g, 5.00 equiv). The resulting solution was stirred for 48 h at 40° C. The mixture was cooled to room temperature and the solid was filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography (silica gel, eluting with EtOAc/petroleum ether (1:20)). This resulted in 0.96 g (30%) the title compound as a light yellow solid. LC/MS: m/z (ES+) 278 (M+H)+. 1H-NMR (300 MHz, DMSO-d6): δ ppm 8.82-8.80 (m, 1H), 8.24 (d, J=7.2 Hz, 1H), 7.95-7.80 (m, 3H), 1.22 (s, 9H).

Workup

customTo a 100-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of argon
temperatureThe mixture was cooled to room temperature
filtrationthe solid was filtered
concentrationThe filtrate was concentrated under reduced pressure
customthe resulting residue was purified by flash column chromatography (silica gel, eluting with EtOAc/petroleum ether (1:20))

Sources & evidence

ORD record: ord-add56652626744cc90856354ef7a324c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181200B2

Reaction notes

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