Thionyl Chloride → HCID 20485604, compound

HRID 647089Notes

Reaction equation

HRID 647089 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])O)[CH:2]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[ClH:15].[Cl:19][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 13236916HCID 13236916, compound

Product 1

HCID 20485604HCID 20485604, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 100 ml Erlenmeyer flask equipped with a reflux condensor is added 2.54 gm of 3-pyridyl-2,4-dichlorophenylcarbinol and 30 ml of chloroform. The system is cooled to 0° C. and 1.31 gm (1.2 equivalents) of thionyl chloride in 25 ml of chloroform is added over 1/2-hour. After addition of the thionyl chloride, the system is allowed to come to room temperature and stirred there for 2 hours. The system is then heated at reflux for 1 hour. The chloroform is removed by stripping to give the alpha-chloro-alpha-(3-pyridyl)-2,4-dichlorotoluene hydrochloride salt.

Workup

  1. customTo a 100 ml Erlenmeyer flask equipped with a reflux condensor
  2. customto come to room temperature
  3. temperatureThe system is then heated
  4. temperatureat reflux for 1 hour
  5. customThe chloroform is removed

Sources & evidence

ORD record
ord-5ec612f6374a4c55a69ec21712a2b13c
Source dataset
uspto-grants-1983_10
Patent number
US04407806

Reaction notes

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