Sodium methanethiolate → 5-Tert-butyl-2-methoxy-1-methylsulphanylmethyl-3-nitro-benzene

HRID 1028437Notes

Reaction equation

[CH3:1][S-:2].[Na+].CS(O[CH2:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[C:11]=1[O:23][CH3:24])(=O)=O>O1CCOCC1>[C:16]([C:14]1[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[C:11]([O:23][CH3:24])=[C:10]([CH2:9][S:2][CH3:1])[CH:15]=1)([CH3:17])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 40 °C

Procedure

At ambient temperature 1.50 g sodium thiomethoxide are added to a solution of 4.64 g 5-tert-butyl-2-methoxy-3-nitro-benzyl methanesulphonate in 50 ml of 1,4-dioxane. The solution is stirred overnight at 40° C. Then the solvent is removed and the residue is chromatographed on silica gel with cyclohexane/ethyl acetate (98:2→60:40) as eluant.

Workup

customThen the solvent is removed
customthe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (98:2→60:40) as eluant

Sources & evidence

ORD record: ord-0eb05a912767402ca2a138ba5e2005f2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735579B2

Reaction notes

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