Ethyl chloroformate → HCID 86717590, compound

HRID 715527

Reaction equation

HRID 715527 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[NH2:10].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[NH:10][C:12](=[O:13])[O:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 2431706-Methoxy-4-methylpyridin-3-amine

Product 1

HCID 86717590HCID 86717590, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL flask was added 4-methyl-6-(methyloxy)-3-pyridinamine (850 mg, 6.15 mmol), pyridine (10 mL) and then ethyl chloroformate (0.650 mL, 6.77 mmol) portionwise. The reaction mixture was stirred for 1 h at 0° C. The reaction mixture was then concentrated and partitioned between ammonium chloride and DCM, and the aqueous layer was extracted with DCM (2×). The combined organics layers were washed with brine (1×), eluted through a phase separator then concentrated to afford ethyl [4-methyl-6-(methyloxy)-3-pyridinyl]carbamate (1.223 g, 90% yield).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ammonium chloride and DCM
  3. extractionthe aqueous layer was extracted with DCM (2×)
  4. washThe combined organics layers were washed with brine (1×)
  5. washeluted through a phase separator
  6. concentrationthen concentrated

Sources & evidence

ORD record
ord-c3e18235a1ff407ebd7487b7b56283d5
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Linked notes

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