Phosgene → HCID 20228142, compound

HRID 1731596Notes

Reaction equation

HRID 1731596 reaction equation
[CH:1]([C:4]1[C:5](=[O:12])[N:6](C)[C:7](S)=[N:8][N:9]=1)([CH3:3])[CH3:2].[C:13]([Cl:16])([Cl:15])=O>C(OCC)(=O)C>[ClH:15].[Cl:16][C:13]1[N:6]([CH3:7])[C:5](=[O:12])[C:4]([CH:1]([CH3:3])[CH3:2])=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 178440400HCID 178440400, compound

Product 1

HCID 20228142HCID 20228142, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

18.6 g (0.1 mole) of 6-isopropyl-3-mercapto-4-methyl-1,2,4-triazin-5(4H)-one are suspended in 100 ml of ethyl acetate. Then 10.9 g (0.11 mole) of phosgene are introduced at room temperature. The ensuing reaction is slightly exothermic. As the reaction is not yet complete, the mixture is stirred for 1 hour at 45° C. The mixture, which is still in the form of a white suspension, is then filtered. The residue is washed with absolute diethyl ether and the resultant white powder is dried in vacuo without heating, affording 20.3 g (90.8% of theory) of 3-chloro-6-isopropyl-4-methyl-1,2,4-triazin-5(4H)-one hydrochloride with a melting point of 144° C. (dec.). The compound sublimes when heated to 45° C. in a high vacuum, yielding the free chloride with a melting point of 129° C. (dec.).

Workup

  1. customThe ensuing reaction
  2. filtrationis then filtered
  3. washThe residue is washed with absolute diethyl ether
  4. customthe resultant white powder is dried in vacuo
  5. temperaturewithout heating

Sources & evidence

ORD record
ord-69d828e12ec34960b50884e8c4d9d42f
Source dataset
uspto-grants-1986_11
Patent number
US04622397

Reaction notes

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