Iodine → HCID 11392086, compound

HRID 2243465Notes

Reaction equation

HRID 2243465 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O-]S([O-])(=O)=O.[Mg+2].[C:22]([C:26]1C=C(O)C(=[CH:31][CH:32]=1)O)(C)([CH3:24])[CH3:23].II>CC(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1[CH:10]=[C:11]2[C:12](=[CH:13][CH:14]=1)[NH:15][C:22]([CH3:24])([CH3:23])[CH:26]=[C:32]2[CH3:31])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 807IodineHCID 73814-tert-ButylcatecholHCID 24083Sulfuric acid magnesium salt (1:1)HCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 11392086HCID 11392086, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-Boc-1,4-phenylenediamine (75 g), MgSO4 (216 g), 4-tert-butylcathechol (1.8 g) and iodine (4.7 g) in anhydrous acetone (600 ml) was heated under reflux for 20 h. The MgSO4 was removed by filtration and the filtrate was concentrated in vacuo. The residue was chromatographed on a short plug of silicagel using heptane/ethyl acetate=8/2 (v/v) as the eluent to give the product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. customThe MgSO4 was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was chromatographed on a short plug of silicagel

Sources & evidence

ORD record
ord-b28891553f9141768667b0cbed5d03ae
Source dataset
uspto-grants-2010_03
Patent number
US07674909B2

Reaction notes

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