Methyl iodide → N-Boc 4-Iodo-N-methylaniline

HRID 1841603Notes

Reaction equation

HRID 1841603 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].I[CH3:17].[H-].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[CH:9]=[CH:10][C:11]([I:14])=[CH:12][CH:13]=1)[CH3:17])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 2773612tert-butyl N-(4-iodophenyl)carbamate

Product 1

HCID 18537740N-Boc 4-Iodo-N-methylanilineYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.96 g (50 mmol) (4-Iodo-phenyl)-carbamic acid tert-butyl ester and 24.96 ml (400 mmol) iodomethane in 250 ml THF was treated at −18° C. with 4.36 (100 mmol) 55% NaH during 1 h. The reaction was warmed up over night to room temperature, neutralized at 0° C. with aqueous 10% KHSO4, evaporated and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to yield 17.8 g (quantitative) of (4-Iodo-phenyl)-methyl-carbamic acid tert-butyl ester, MS: 333 (M).

Workup

  1. customevaporated
  2. extractionextracted with aqueous 10% KHSO4/Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-573e15aaa2784b7db1d752760662df1d
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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