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

HRID 746752Notes

Reaction equation

HRID 746752 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>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

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 736476tert-Butyl thiophen-3-ylcarbamate

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-thiophenyl)carboxamide (21.0 g, 0.1 mol) in methylene chloride (400 mL) add N-iodosuccinimide (23.7 g, 0.1 mol) in small portions. Set the heating bath to 65° C. for 20 min. Take the reaction to room temperature, evaporate the solvent and purify the crude by flash chromatography (Silica gel-Hexane/EtOAc 9:1) to obtain 30.0 g (88%) of (tert-Butoxy)-N-(2-iodo(3-thiophenyl))carboxamide as a white solid.

Workup

  1. customto 65° C.
  2. customfor 20 min
  3. customthe reaction to room temperature
  4. customevaporate the solvent
  5. custompurify the crude by flash chromatography (Silica gel-Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-ae1c3fb3dcf04ae38b1a72e5b9c242cb
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

Loading…