Methyl iodide → HCID 54189649, compound

HRID 1886380Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])[CH:5]=[N:6][CH:7]=1.CC(C)([O-])C.[K+].[C:21](=[S:23])=[S:22].[CH3:24]I>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:21]([S:23][CH3:24])=[S:22])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 2-(5-bromopyrid-3-yl)cyclohexanone (1.28 g, 5.05 mmol) in dry tetrahydrofuran (35 ml) at -40° C. was added portionwise with stirring potassium tert. butoxide (0.61 g, 5.4 mmol). The reaction mixture was stirred for 1 hour at -40° C. and a solution of carbon disulphide (0.5 ml) in dry tetrahydrofuran (5 ml) was added and the reaction mixture allowed to warm up to -20° C. over 20 minutes. A solution of methyl iodide (1.03 g) in dry tetrahydrofuran (5 ml) was added dropwise and the solution stirred at room temperature for 6 hours. The reaction mixture was concentrated in vacuo, treated with water (25 ml) and extracted with dichloromethane (2×25 ml). The extract was washed with water, dried over magnesium sulphate and concentrated to give 2-(5-bromopyrid-3-yl)-2-methylthiothiocarbonylcyclohexanone as an orange oil 1.33 g. NMR (CDCl3) 1.6-2.1(m,4H); 2.26-2.35(m,2H); 2.6 (s,3H); 2.65-2.9(m.1H); 3.4-3.5(m,1H), 7.84-7.86(dd,1H); 8.54-8.6(dd,2H).

Workup

temperatureto warm up to -20° C. over 20 minutes
stirringthe solution stirred at room temperature for 6 hours
concentrationThe reaction mixture was concentrated in vacuo
additiontreated with water (25 ml)
extractionextracted with dichloromethane (2×25 ml)
washThe extract was washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-a11c34f77a8a414595c6c6e7d76d397f
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05151436

Reaction notes

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