Morpholine → 2-(Ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzonitrile

HRID 515151Notes

Reaction equation

Cl[C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4]([S:11]([CH2:13][CH3:14])=[O:12])[CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[CH2:13]([S:11]([C:4]1[CH:3]=[C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:9]=[C:8]([CH3:10])[C:5]=1[C:6]#[N:7])=[O:12])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

4-Chloro-2-(ethylsulfinyl)-6-methyl-benzonitrile (0.31 g, 1.36 mmol), morpholine (0.36 ml, 4.09 mmol) and potassium carbonate (0.24 g, 1.77 mmol) are taken up in N-methyl-2-pyrrolidone (3 ml) in a sealed tube and the resulting mixture is heated at 100° C. for 16 h. The mixture is then diluted with water (6 ml) and extracted with ethyl acetate (3×10 ml). The organic layer is washed with water (2×10 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 50% ethyl acetate/hexane) to yield 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzonitrile (0.22 g, 0.79 mmol, 58%).

Workup

extractionextracted with ethyl acetate (3×10 ml)
washThe organic layer is washed with water (2×10 ml), brine (20 ml)
dry with materialdried over anhydrous sodium sulfate
customevaporated
customto get the crude product, which
customis purified by column chromatography (silica gel, 50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-fe49e75035a64c8f8da9247baf5c6c18
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108936B2

Reaction notes

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