Sodium ethoxide → Ethyl (6-ethoxy-4-methylpyridazin-3-yl)carbamate

HRID 715535Notes

Reaction equation

HRID 715535 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:4]([CH3:14])[CH:3]=1.[O-:15][CH2:16][CH3:17].[Na+]>>[CH2:16]([O:15][C:2]1[N:7]=[N:6][C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:4]([CH3:14])[CH:3]=1)[CH3:17]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 86717594Ethyl (6-chloro-4-methylpyridazin-3-yl)carbamate

Product 1

HCID 86717595Ethyl (6-ethoxy-4-methylpyridazin-3-yl)carbamateYield 69.3%

Conditions

Temperature
110 °C

Procedure

A 20 mL microwavable vial was charged with ethyl (6-chloro-4-methylpyridazin-3-yl)carbamate (550 mg, 2.55 mmol) and sodium ethoxide (3.11 mL, 17.85 mmol), then stirred and heated at 110° C. for 12 h. The reaction mixture was then concentrated and partitioned between ammonium chloride and DCM. The layers were separated and the aqueous layers were washed with DCM (2×). The combined organic layers were washed with water, brine, and eluted through a phase separator. The organic layers were concentrated to afford ethyl (6-ethoxy-4-methylpyridazin-3-yl)carbamate (398 mg, 65.8% yield).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ammonium chloride and DCM
  3. customThe layers were separated
  4. washthe aqueous layers were washed with DCM (2×)
  5. washThe combined organic layers were washed with water, brine
  6. washeluted through a phase separator
  7. concentrationThe organic layers were concentrated

Sources & evidence

ORD record
ord-760ade482e334f1bbd6ea0b30300b5a0
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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