Iodine → HCID 19068902, compound

HRID 1957125Notes

Reaction equation

HRID 1957125 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[I:13]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([I:13])[C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 807IodineHCID 814454,5-Dimethyl-2-nitrobenzenamine

Product 1

HCID 19068902HCID 19068902, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Silver sulphate (103 g, 0.33 mol) was added over 5 minutes to a stirred suspension of 4,5-dimethyl-2-nitroaniline (50.0 g, 0.30 mol) in ethanol (1500 mL) at 20° C. Iodine (84.0 g, 0.33 mol) was added in portions, and the resulting mixture was stirred for 30 minutes at 20° C. The mixture was filtered, and the filter cake washed thoroughly with ethanol (1 L) and dichloromethane (1 L). The filtrate was concentrated under reduced pressure, and the residue was redissolved in dichloromethane (500 mL), and washed with 10% aqueous sodium metabisulphite (2×500 mL), and brine (250 mL). The solution was dried (MgSO4) and concentrated under reduced pressure to give 4,5-dimethyl-6-iodo-2-nitroaniline (82.1 g, 93%) as an orange solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed thoroughly with ethanol (1 L) and dichloromethane (1 L)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was redissolved in dichloromethane (500 mL)
  5. washwashed with 10% aqueous sodium metabisulphite (2×500 mL), and brine (250 mL)
  6. dry with materialThe solution was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8df3786c1cb4c03b036f9d7b0770edd
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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