Sodium Iodide → 2-Iodo-N-[3,4-bis(phenylmethoxy)phenyl]acetamide

HRID 4113Notes

Reaction equation

HRID 4113 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1)=[O:4].[I-:28].[Na+]>CC(C)=O>[I:28][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 201534662-Chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide

Product 1

HCID 201534732-Iodo-N-[3,4-bis(phenylmethoxy)phenyl]acetamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide (8.98 g, 23.5 mmol) and sodium iodide (3.53 g, 23.5 mmol) in acetone (75 ml) was refluxed for two hours and allowed to stand overnight at room temperature. The reaction was filtered hot to remove the sodium iodide and a precipitate formed in the cold filtrate which was collected and washed with cold acetone to give, upon drying, 6.71 g (14.2 mmol) of the title compound. A second crop was obtained from cold acetone (1.0 g).

Workup

  1. filtrationThe reaction was filtered hot
  2. customto remove the sodium iodide
  3. customa precipitate formed in the cold filtrate which
  4. customwas collected
  5. washwashed with cold acetone
  6. customto give
  7. customupon drying

Sources & evidence

ORD record
ord-b6175eeac55148129b4ba8d24ceb3f10
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Reaction notes

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