N-Iodosuccinimide → HCID 178522276, compound

HRID 2283472Notes

Reaction equation

HRID 2283472 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1C(=O)N([I:26])C(=O)C1>C(Cl)Cl>[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]([I:26])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178522213HCID 178522213, compound

Product 1

HCID 178522276HCID 178522276, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (2-hydroxypyridin-3-yl)carbamate (16.1 g, 65.9 mmol) in DCM (500 mL) was added NIS (17.8 g, 79.1 mmol) and the mixture heated at reflux overnight. After cooling, the mixture was filtered to afford benzyl (2-hydroxy-5-iodopyridin-3-yl)carbamate (16 g, 65% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.72 (s, 1H), 7.29-7.40 (m, 5H), 5.21 (s, 2H); MS (ES) m/z 370 (M+H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-bc1ecfc34a0b4e7eb537f3f5c8ab71d7
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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