Ethyl Acetate → 2-Chloro-4-methyl-3-pyridylisocyanate

HRID 726805Notes

Reaction equation

HRID 726805 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[C:10](OCC)(=[O:12])C>>[Cl:9][C:3]1[C:2]([N:1]=[C:10]=[O:12])=[C:7]([CH3:8])[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 27563873-Amino-2-chloro-4-methylpyridine

Product 1

HCID 197079832-Chloro-4-methyl-3-pyridylisocyanate

Procedure

3-Amino-2-chloro-4-methylpyridine (4.3 g) was added to a solution of trichloro-methyl chloformate (6.0 g) in ethyl acetate (100 ml) at 0° to 5° C. with stirring and the mixture was refluxed under heating for 6 hours. After removal of the solvent under reduced pressure, 2-chloro-4-methyl-3-pyridylisocyanate (4.9 g) was obtained. A mixture of 2-chloro-4-methyl-3-pyridylisocyanate (4.9 i) and trimethylsilyl azide (11 g) was refluxed under heating for 30 hours. After removal of excess trimethylsilyl azide under reduced pressure, methanol was added to the resulting residue. Thereafter, the methanol was distilled off under reduced pressure. The resulting residue was purified by flash column chromatography (eluent chloroform:ethanol=15:1) to obtain the desired 1-(2-chloro-4-methyl-3-pyridyl)-5(4H)-tetrazolinone (3.0 g). m.p. 160°-162° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6 hours
  3. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6b793ebda44145d58e00ba5a3b49552f
Source dataset
uspto-grants-1998_01
Patent number
US05710278

Reaction notes

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