Ether hydrochloride → (4-Azido-3-iodophenyl)methanamine hydrochloride

HRID 1961488Notes

Reaction equation

HRID 1961488 reaction equation
[N:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9]C(=O)OC(C)(C)C)=[CH:6][C:5]=1[I:19])=[N+:2]=[N-:3].O(CC)CC.[ClH:25]>>[ClH:25].[N:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH2:9])=[CH:6][C:5]=1[I:19])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 10953452Ether hydrochlorideHCID 86661980tert-Butyl 4-azido-3-iodobenzylcarbamate

Product 1

HCID 86661981(4-Azido-3-iodophenyl)methanamine hydrochlorideYield 45%

Procedure

tert-Butyl 4-azido-3-iodobenzylcarbamate (936.0 mg, 2.5 mmol) was dissolved in Et2O.HCl (2.0 N in Et2O) (10 ml) was added to the solution. The mixture was stirred at r.t. overnight. The solvent was removed under vacuum and the residue washed with a mixture of CH2Cl2 and MeOH (8:2) affording 350 mg (45%) of the title compound.

Workup

  1. additionwas added to the solution
  2. customThe solvent was removed under vacuum
  3. washthe residue washed with a mixture of CH2Cl2 and MeOH (8:2)

Sources & evidence

ORD record
ord-373f551e086a4231bdfd939c8284ff61
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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