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

HRID 506954Notes

Reaction equation

HRID 506954 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1[C:12](=[O:17])[NH:13][CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:26])C(=O)C1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1[C:12](=[O:17])[NH:13][CH:14]=[C:15]([I:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 12045578Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate

Product 1

HCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamateYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Oxo-1,2-dihydro-pyridin-3-yl)-carbamic acid benzyl ester (410 g, 1.68 mol, 1.0 Eq.) was charged to a flask followed by DCM (6.6 L) and NIS (378 g, 1.68 mol, 1.0 Eq.). The reaction was then allowed to stir at ambient temperature overnight. Tlc analysis showed starting material was still present, therefore a further amount of NIS (25 g, 0.11 mmol, 0.07 Eq.) was added and the reaction stirred for a further 3 hours. NMR analysis of the reaction showed 87% conversion, therefore the reaction mixture was filtered and the red solid washed with DCM (2 L) and Et2O (2 L). The solid was then slurried in dilute aqueous sodium thiosulfate solution (2 g in 2 L), filtered, and then slurried twice in water (2×1.5 L). The pale pink solid was dried on the filter and then in vacuo at 50° C. overnight to give the desired product as a pale pink solid (287 g, 775 mmol, 46%)

Workup

  1. stirringthe reaction stirred for a further 3 hours
  2. filtrationthe reaction mixture was filtered
  3. washthe red solid washed with DCM (2 L) and Et2O (2 L)
  4. filtrationfiltered
  5. customThe pale pink solid was dried on the
  6. filtrationfilter

Sources & evidence

ORD record
ord-f9205d06d59044b280ecc789eee26f31
Source dataset
uspto-grants-2010_08
Patent number
US07786130B2

Reaction notes

Loading…