Cesium carbonate → trans-N-cyanomethyl-2-(4-methylsulfanylphenylsulfanylmethyl)-Cyclohexanecarboxamide

HRID 2222900Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13]Br)=[O:6])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][S:22][C:23]1[CH:28]=[CH:27][C:26]([SH:29])=[CH:25][CH:24]=1>CC(C)=O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:29][C:26]1[CH:27]=[CH:28][C:23]([S:22][CH3:21])=[CH:24][CH:25]=1)=[O:6])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

trans-2-Bromomethyl-cyclohexanecarboxylic acid cyanomethyl-amide (258 mg) and cesium carbonate (329 mg) were weighed into a 15 mL vial fitted with a stir bar and a vent cap. Acetone (3 mL) and 4-(methylsulfanyl)thiophenol (162 mg) were added. The reaction mixture was stirred at 50° C. overnight and then diluted with hot acetone (7 mL) and filtered through Celite™. The Celite™ was washed with hot acetone. The filtrate and wash were combined and the solvent was removed on a rotary evaporator. Chromatography of the crude product on a silica gel (using 9:1 dichloromethane: acetone as the eluent) provided the title compound as a white solid. 1H NMR (DMSO-d6): δ=8.63 (1H, t), 7.24 (2H, d), 7.18 (2H, d), 4.13 (2H, d), 2.97 (1H, dd), 2.58 (1H, m), 2.96 (3H, s), 2.1 (2H, m), 1.7 (4H, m), 1.2 (4H, m) MS [ESI, (M−H)−] m/z=332.8 amu

Workup

customvial fitted with a stir bar
customa vent cap
filtrationfiltered through Celite™
washThe Celite™ was washed with hot acetone
washThe filtrate and wash
customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record: ord-de435ef5d5fd4a60aa9c589a9eb19107
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371747B2

Reaction notes

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