Water → Methyl 6-isocyanatopyridazine-3-carboxylate

HRID 624206Notes

Reaction equation

HRID 624206 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.O>C1(C)C=CC=CC=1>[N:1]([C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)=[C:20]=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 14536428Methyl 6-aminopyridazine-3-carboxylate

Product 1

HCID 86665081Methyl 6-isocyanatopyridazine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To the solution of methyl 6-aminopyridazine-3-carboxylate (14 g, 91.5 mmol) in anhydrous toluene (700 mL) was added Et3N (11.1, 109.8 mmol). A solution of triphosgene (27.2 g, 91.5 mmol) in anhydrous toluene was added slowly at 0° C. The reaction mixture was stirred for 2 hrs at room temperature and then heated at 90° C. for 5 hrs. After cooling to room temperature, toluene and water were added to the mixture, the mixture was separated and the organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to give the title compound as a solid.

Workup

  1. temperatureheated at 90° C. for 5 hrs
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was separated
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9df310a43324073963e6c71e30a482f
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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