N-Iodosuccinimide → Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

HRID 1725631Notes

Reaction equation

HRID 1725631 reaction equation
[I:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[C:15]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=[CH:12][NH:11]1>ClCCl>[I:1][C:13]1[CH:14]=[C:15]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10](=[O:9])[NH:11][CH:12]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 12045578Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate

Product 1

HCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamateYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Iodosuccinimide (0.292 g, 1.30 mmol) was added to a solution of benzyl 2-oxo-1,2-dihydropyridin-3-ylcarbamate (0.317 g, 1.3 mmol) in anhydrous dichloromethane (10 mL) and stirred overnight. The mixture was concentrated and purified by chromatography [silica gel, 0% to 50% ethyl acetate in hexanes gradient elution] to give the title compound (0.245 g). MS 371 (M+1)

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography [silica gel, 0% to 50% ethyl acetate in hexanes gradient elution]

Sources & evidence

ORD record
ord-72ad1da289f14b25955e707eefd17f9e
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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