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

HRID 2360513Notes

Reaction equation

HRID 2360513 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:9]([N+:17]([O-:19])=[O:18])[C:8]=1[O:20][CH3:21])(=O)=O.[CH3:22][S-:23].[Na+]>O1CCOCC1>[C:13]([C:11]1[CH:10]=[C:9]([N+:17]([O-:19])=[O:18])[C:8]([O:20][CH3:21])=[C:7]([CH2:6][S:23][CH3:22])[CH:12]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 584939545-Tert-butyl-2-methoxy-3-nitro-benzyl methanesulphonate

Product 1

HCID 584939255-Tert-butyl-2-methoxy-1-methylsulphanylmethyl-3-nitro-benzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.64 g 5-tert-butyl-2-methoxy-3-nitro-benzyl methanesulphonate are dissolved in 50 ml of 1,4-dioxane, combined with 950 mg of sodium thiomethanolate and stirred for 12 hours at ambient temperature. A further 600 mg of sodium thiomethoxide are added and the mixture is stirred for 2 hours at 40° C. Then the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 98:2 to 60:40).

Workup

  1. stirringthe mixture is stirred for 2 hours at 40° C
  2. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 98:2 to 60:40)

Sources & evidence

ORD record
ord-d3d765ab33b24118934fb3585c116c53
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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