Thionyl Chloride → 3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dione

HRID 868310Notes

Reaction equation

HRID 868310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)O.S(Cl)([Cl:27])=O>ClC(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([Cl:27])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1351082-(3-Chloro-4-((4-chlorophenyl)hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 225573573-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dioneYield 83.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 16 parts of 2-[3-chloro-4-[(4-chlorophenyl)hydroxymethyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione and 150 parts of trichloromethane were added dropwise, during a period of 5 minutes, 16 parts of thionyl chloride. Upon completion, stirring was continued for 3 hours at reflux temperature. The reaction mixture was evaporated in vacuo. Methylbenzene was added and the whole was evaporated again, yielding 14 parts (83.1%) of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione as a residue (intermediate 107).

Workup

  1. additionwere added dropwise, during a period of 5 minutes
  2. temperatureat reflux temperature
  3. customThe reaction mixture was evaporated in vacuo
  4. additionMethylbenzene was added
  5. customthe whole was evaporated again

Sources & evidence

ORD record
ord-8e71594f8d414768a6b8db52cfc0e7d1
Source dataset
uspto-grants-1988_10
Patent number
US04778887

Reaction notes

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