Thionyl Chloride → Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

HRID 1841441Notes

Reaction equation

HRID 1841441 reaction equation
O[C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].S(Cl)([Cl:17])=O>>[Cl:17][C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178470469HCID 178470469, compound

Product 1

HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

Conditions

Temperature
75 °C

Procedure

To 17.0 g (78.98 mmol) of 5-hydroxy-3-methylsulfanyl-1,2,4-triazine-6-carboxylic acid, ethyl ester was added 86 mL (1184.7 mmol) of thionyl chloride. The reaction mixture was heated to 75° C. for 2 hours, cooled, and concentrated. The residue was twice suspended in toluene and concentrated to give a yellow-orange solid, 5-chloro-3-methylsulfanyl-1,2,4-triazine-6-carboxylic acid, ethyl ester.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a6396f04fe7443de8d020e88d61bcf95
Source dataset
uspto-grants-2004_01
Patent number
US06683183B2

Reaction notes

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