Thionyl Chloride → HCID 21435955, compound

HRID 1076540Notes

Reaction equation

HRID 1076540 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:20])=[O:7])=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 137504764-Chloro-2-(phenylsulfanyl)benzoic acid

Product 1

HCID 21435955HCID 21435955, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred suspension of 59.2 g. (0.224 mole) of 4-chloro-2-(phenylthio)benzoic acid in 200 ml. of benzene is added dropwise 41.6 g. (0.35 mole) of thionyl chloride during a 1 hour period, and the reaction mixture is heated under reflux for an additional hour. The reaction mixture is then concentrated to dryness under reduced pressure, and the residue is recrystallized from 300 ml. of boiling hexane to yield 41.9 g. of pale yellow product, melting point 94°-96°C.

Workup

  1. additionTo a stirred suspension of 59.2 g
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for an additional hour
  4. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure
  5. customthe residue is recrystallized from 300 ml
  6. customof boiling hexane to yield 41.9 g

Sources & evidence

ORD record
ord-755e437d26da4c5da6ebe1fc405ca086
Source dataset
uspto-grants-1976_05
Patent number
US03957769

Reaction notes

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