Sodium Hydroxide → Methyl (4-iodo-5-methylpyridin-2-yl)carbamate

HRID 537032Notes

Reaction equation

HRID 537032 reaction equation
[CH3:1][O:2][C:3]([N:5]([C:10]1[CH:15]=[C:14]([I:16])[C:13]([CH3:17])=[CH:12][N:11]=1)C(OC)=O)=[O:4].[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:4])[NH:5][C:10]1[CH:15]=[C:14]([I:16])[C:13]([CH3:17])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66748316Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate

Product 1

HCID 67952848Methyl (4-iodo-5-methylpyridin-2-yl)carbamateYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate (110 g, 310 mmol) was added to a mixture of MeOH (1500 mL) and 1M NaOH (620 mL). The reaction mixture was allowed to stir at rt for 1.5 h and was then concentrated. EtOAc and water were added to the residue and the solution was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give methyl(4-iodo-5-methylpyridin-2-yl)carbamate (68 g, 60%) which was used in the next step without purification.

Workup

  1. concentrationwas then concentrated
  2. additionEtOAc and water were added to the residue
  3. extractionthe solution was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8de1e3babf17429e99ca7dcda2c8e749
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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