Isoamyl Nitrite → 5-Tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene

HRID 2360511Notes

Reaction equation

HRID 2360511 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([O:12][CH3:13])=[C:9](N)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(ON=O)CC(C)C.[CH3:25][S:26]SC>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([O:12][CH3:13])=[C:9]([S:26][CH3:25])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 12232Dimethyl DisulfideHCID 112068635-(tert-Butyl)-2-methoxy-3-nitroaniline

Product 1

HCID 584939295-Tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g 5-tert-butyl-2-methoxy-3-nitro-phenylamine are dissolved in 20 ml acetonitrile, combined successively with 3.6 ml isopentylnitrite as well as 2.4 ml dimethyldisulphide and refluxed for 2 h. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (petroleum ether/ethyl acetate 90:10).

Workup

  1. temperaturerefluxed for 2 h
  2. customthe residue is chromatographed on silica gel (petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-26183b1c99964a2bbba39c3fccd96cb7
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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