Methyl iodide → benzyl N-(4-iodophenyl)-N-methylcarbamate

HRID 1018006Notes

Reaction equation

HRID 1018006 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21]I>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]([CH3:21])[C:12]1[CH:13]=[CH:14][C:15]([I:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1245679N-Cbz-4-iodoaniline

Product 1

HCID 18404743benzyl N-(4-iodophenyl)-N-methylcarbamateYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of N-benzyloxycarbonyl-4-iodoaniline (11.5 g, Reference Example 27) in dimethylformamide (70 ml) was treated portionwise with sodium hydride (⅙ g of a 60% dispersion in oil), under nitrogen and at room temperature. When effervescence had ceased methyl iodide (6.3 g) was added and the mixture was stirred at room temperature for 2 hours, after which it was partitioned between ethyl acetate and water. The organic phase was separated, then dried over magnesium sulphate and then evaporated to give the title compound (11.5 g) as a pink oil.

Workup

  1. customat room temperature
  2. additionwas added
  3. customafter which it was partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-da2c498bf9dc44d797f26ef8ea60d3f8
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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