Sodium Hydroxide → HCID 86699729, compound

HRID 515152Notes

Reaction equation

[CH2:1]([S:3]([C:5]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8])=[O:4])[CH3:2].[OH-:20].[Na+]>C(O)C.O>[CH2:1]([S:3]([C:5]1[CH:12]=[C:11]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]([NH2:8])=[O:20])=[O:4])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzonitrile (0.78 g, 2.81 mmol) in ethanol (8.5 ml) is added a 5M solution of sodium hydroxide (8.5 ml) and the mixture is heated at 80° C. for 16 h. After completion of the reaction (monitored by TLC) the reaction mixture is concentrated to get a residue, which is diluted with water (10 ml) and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (10 ml), brine (10 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product which is purified by column chromatography (alumina, 5% methanol/dichloromethane) to yield 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzamide (0.30 g, 1.01 mmol, 36%).

Workup

customAfter completion of the reaction (monitored by TLC) the reaction mixture
concentrationis concentrated
customto get a residue, which
extractionextracted with ethyl acetate (3×30 ml)
washThe combined organic layers are washed with water (10 ml), brine (10 ml)
dry with materialdried over anhydrous sodium sulfate
customevaporated
customto get the crude product which
customis purified by column chromatography (alumina, 5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-8e38fc6cf27045dda609869e54512c8b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108936B2

Reaction notes

Loading…