Methyl chloroformate → Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate

HRID 537031Notes

Reaction equation

HRID 537031 reaction equation
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:22])[O:20][CH3:21]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:21][O:20][C:19]([N:9]([C:4]1[CH:3]=[C:2]([I:1])[C:7]([CH3:8])=[CH:6][N:5]=1)[C:19]([O:20][CH3:21])=[O:22])=[O:22]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 667478634-Iodo-5-methylpyridin-2-amine

Product 1

HCID 66748316Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonateYield 82.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-iodo-5-methylpyridin-2-amine (90 g, 380 mmol) in DCM (3800 mL) were added DIEA (192 mL, 930 mmol) and methyl carbonochloridate (58.8 mL, 760 mmol) at 0° C. The reaction mixture was allowed to stir at 0° C. for 1 h and was then diluted with aqueous saturated NH4Cl. The organic solvent was separated and the aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine and concentrated to give dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate (110 g, 80%) which was used in the next step without purification.

Workup

  1. customThe organic solvent was separated
  2. extractionthe aqueous solution was extracted with DCM
  3. washwashed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6959c635703c404d9483d1aa579afcd7
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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