Acetic Anhydride → N-(4-iodobenzyl)acetamide

HRID 330828Notes

Reaction equation

HRID 330828 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[I:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1>C(O)(=O)C>[I:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:14][C:5](=[O:7])[CH3:6])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27375334-Iodobenzylamine

Product 1

HCID 23111624N-(4-iodobenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.34 mL (3.5 mmol) acetic anhydride are added to 750 mg (3.22 mmol) 4-iodo-benzylamine in 15 ml acetic acid and the mixture is stirred at rt for 4 h. After that time, the solvent is evaporated and the residue partitionated between TBME and water. The organic layer is separated, washed with water (1×) and saturated NaHCO3 solution (2×). The organic layer is dried over sodium sulphate and the solvent is evaporated to yield the desired product.

Workup

  1. customAfter that time, the solvent is evaporated
  2. customThe organic layer is separated
  3. washwashed with water (1×) and saturated NaHCO3 solution (2×)
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d4becb1bd9bc4f64b47b0e4644f053dc
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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