Ethyl chloroformate → Ethyl (6-chloro-4-methylpyridazin-3-yl)carbamate

HRID 715534Notes

Reaction equation

HRID 715534 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][C:11](=[O:12])[O:13][CH2:14][CH3:15])=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 123536646-Chloro-4-methylpyridazin-3-amine

Product 1

HCID 86717594Ethyl (6-chloro-4-methylpyridazin-3-yl)carbamateYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL flask was charged with 6-chloro-4-methylpyridazin-3-amine (700 mg, 4.88 mmol) and pyridine (20 mL) then ethyl chloroformate (0.421 mL, 4.39 mmol) was added 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. The aqueous layer was extracted with DCM (2×). The organic layers were combined and washed with brine (1×), eluted through a phase separator and concentrated to afford ethyl (6-chloro-4-methylpyridazin-3-yl)carbamate (549 mg, 49.6% 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. washwashed with brine (1×)
  5. washeluted through a phase separator
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db37325d408a41d98a6fc68e47ca942b
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

Loading…