Dichloromethane → Methyl 3-[(methylamino)carbonothioyl]-5-(5-methylpyridin-2-yl)benzoate

HRID 888382Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:31]2)=CC=1.ClCCl>ClC(Cl)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[S:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate (2.90 g, 10.2 mmol) in dichloroethane (20 mL) was added 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson's reagent) (2.27 g, 5.61 mmol) and the mixture heated to 60° C. After 2 h, the reaction was cooled to ambient temperature. Dichloromethane (200 mL) was added, and the mixture washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) to give the title compound (1.9 g). MS 301.0 (M+1).

Workup

temperaturethe reaction was cooled to ambient temperature
washthe mixture washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record: ord-489f178967c74f31a6286d3efdce309d
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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