Morpholine → N-(Morpholine-4-carbothioyl)benzenecarboximidic acid

HRID 541343Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([N:15]=[C:16]=[S:17])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(C)=O>[N:1]1([C:16]([NH:15][C:7](=[O:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[S:17])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 50-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was added a solution of morpholine (1.00 g, 11.5 mmol, 1.00 equiv) in acetone (10 mL). TEA (1.74 g, 17.2 mmol, 1.50 equiv) was added to the reaction, and the resulting solution was stirred for 30 min at 25° C. Benzoyl isothiocyanate (1.87 g, 11.5 mmol, 2.00 equiv) was added dropwise to the reaction at 0° C. The resulting solution was stirred for 30 min at 0° C., then quenched with 20 mL of water. The mixture was extracted with 2×30 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:10-1:3) as eluent to furnish 2.30 g (80%) of N-(morpholine-4-carbonothioyl)benzamide as a yellow solid.

Workup

customTo a 50-mL three neck round-bottom flask, which was purged
temperaturemaintained with an inert atmosphere of nitrogen
stirringThe resulting solution was stirred for 30 min at 0° C.
customquenched with 20 mL of water
extractionThe mixture was extracted with 2×30 mL of ethyl acetate
dry with materialThe combined organic layers were dried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-94c8f4d4b8344804923ab1c592dced72
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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