Thionyl Chloride → Chloro[2-(2,4,6-trichlorophenyl)hydrazinylidene]acetyl chloride

HRID 435578Notes

Reaction equation

HRID 435578 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][N:11]=[C:12]([Cl:16])[C:13](O)=[O:14].S(Cl)([Cl:19])=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][N:11]=[C:12]([Cl:16])[C:13]([Cl:19])=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 857936332-Chloro-2-[2-(2,4,6-trichlorophenyl)hydrazinylidene]acetic acid

Product 1

HCID 71365096Chloro[2-(2,4,6-trichlorophenyl)hydrazinylidene]acetyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture consisting of 61 g. (0.20 mole) chloroglyoxylic acid (2,4,6-trichlorophenyl)hydrazone, 200 ml. carbon tetrachloride, and 100 ml. thionyl chloride was heated at the reflux temperature for 6 1/2 hrs. The carbon tetrachloride and thionyl chloride were removed by evaporation under reduced pressure and 50° C. to give 64 g. of an oil. The oil was extracted with technical hexane and the insoluble starting material was removed by filtration. The technical hexane was removed by evaporation under reduced pressure to give chloroglyoxyloyl chloride (2,4,6-trichlorophenyl) hydrazone.

Workup

  1. customThe carbon tetrachloride and thionyl chloride were removed by evaporation under reduced pressure and 50° C.
  2. customto give 64 g
  3. extractionThe oil was extracted with technical hexane
  4. customwas removed by filtration
  5. customThe technical hexane was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ff31609494244da689df6cb9df14335d
Source dataset
uspto-grants-1977_02
Patent number
US04006132

Reaction notes

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