N-Iodosuccinimide → N-(2-iodothiophen-3-yl)-2-(naphthalen-1-yl)acetamide

HRID 1519971Notes

Reaction equation

HRID 1519971 reaction equation
[C:1]1([CH2:11][C:12]([NH:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[I:20]N1C(=O)CCC1=O>C(#N)C>[I:20][C:16]1[S:17][CH:18]=[CH:19][C:15]=1[NH:14][C:12](=[O:13])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 687555152-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide

Product 1

HCID 68754386N-(2-iodothiophen-3-yl)-2-(naphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide (7.50 g, 28.1 mmol) and N-iodosuccinimide (7.12 g, 31.6 mmol) in acetonitrile (100 ml) was placed into a preheated oil bath at 75° C. After stirring for 18 h, the solution was concentrated under reduced pressure. The residue was flash chromatographed with 99:1, 49:1, 24:1, and 23:2 methylene chloride:ethyl acetate as the eluant to yield impure N-(2-iodothiophen-3-yl)-2-(naphthalen-1-yl)acetamide. Method [1] Retention time 2.32 min by HPLC (MH+ 394).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customchromatographed with 99:1, 49:1, 24:1, and 23:2 methylene chloride

Sources & evidence

ORD record
ord-141d87ce46ba471fad1f1fd06c60b61b
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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