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

HRID 1684484Notes

Reaction equation

HRID 1684484 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 trichloromethyl 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 g) 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). n.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-236c781fdf3841f2ab77aa22c5eaee62
Source dataset
uspto-grants-1997_06
Patent number
US05641727

Reaction notes

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