Iodine → HCID 10802330, compound

HRID 604600Notes

Reaction equation

HRID 604600 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[I:12]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:9])=[C:10]([I:12])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 807IodineHCID 698614-Tert-Butylaniline

Product 1

HCID 10802330HCID 10802330, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent2×

Procedure

A solution of commercially available 4-tert-butylaniline (2.00 g, 13.4 mmol) in MeOH (10 mL) was added to a mixture of silver sulfate (4.17 g, 13.4 mmol) and iodine (3.39 g, 13.4 mmol) in MeOH (30 mL). The mixture was stirred at room temperature for 4 h. The mixture was filtered. The filtrate was concentrated. The title compound was obtained after flash chromatography using EtOAc:hexane/2:8 as the eluant. 1H NMR (CDCl3, 500 MHz): B7.65 (d, J=2. Hz, 1H), 7.20 (dd, J=8.5, 2.5 Hz, 1H), 6.75 (d, J=8.5 Hz, 1H), 1.30 (s, 9H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-275d19d2324b4965b4dce24dc1b837ef
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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