N-Iodosuccinimide → TERT-BUTYL 2-IODOTHIOPHEN-3-YLCARBAMATE

HRID 1865035Notes

Reaction equation

HRID 1865035 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:14]N1C(=O)CCC1=O.CCCCCC.CCOC(C)=O>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[I:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 736476tert-Butyl thiophen-3-ylcarbamateHCID 21226206Ethyl acetate hexane

Product 1

HCID 11034707TERT-BUTYL 2-IODOTHIOPHEN-3-YLCARBAMATEYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner analogous to Campaigne, E. and Monroe, P. A. J.A.C.S., 76, 2447-2450 (1954), to a boiling solution of (tert-butoxy)-N-(3-thienyl)carboxamide (21.0 g, 0.1 mol, preparation 5) in methylene chloride (400 mL) is added N-iodosuccinimide (23.7 g, 0.1 mol) in small portions. The heating bath is then set to 65° C. for 20 min. TLC (Hexane/AcOEt 9:1) shows complete consumption of starting material. The reaction is taken to room temperature, the solvent is evaporated and the crude is purified by flash chromatography (Silica gel-Hexane/EtOAc 9:1) to obtain 30.0 g (88%) of title compound as a white solid.

Workup

  1. customconsumption of starting material
  2. customis taken to room temperature
  3. customthe solvent is evaporated
  4. customthe crude is purified by flash chromatography (Silica gel-Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-5a6dda2e78294a57ae033d9c12a9726f
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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