Dichloromethane → HCID 15335241, compound

HRID 1005297Notes

Reaction equation

HRID 1005297 reaction equation
[C:1]([CH2:4][S:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])([OH:3])=[O:2].S(Cl)(Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3].[CH2:24](Cl)Cl>>[C:1]([CH2:4][S:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:24])=[O:10])([OH:3])=[O:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 18791048HCID 18791048, compound

Product 1

HCID 15335241HCID 15335241, compound

Conditions

Temperature
20 °C

Procedure

14.3 g (0.06 mmol) of 3-carboxymethylthio-2-methylbenzoic acid are dissolved in 300 ml of methylene chloride and 13.1 g (0.11 mmol) of thionyl chloride are added dropwise. The mixture is refluxed for 1 hour and the solvent and excess thionyl chloride are then distilled off. The residue is taken up in 100 ml of methylene chloride and treated with 31.8 g (0.24 mmol) of aluminum trichloride. The reaction is stirred at about 20° C. for 1 hour. The mixture is then added to ice-water and the organic phase is separated off. After washing and drying the organic phase, the solvent is removed. The product is reacted further without purification.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. distillationthe solvent and excess thionyl chloride are then distilled off
  3. customthe organic phase is separated off
  4. washAfter washing
  5. customdrying the organic phase
  6. customthe solvent is removed
  7. customThe product is reacted further without purification

Sources & evidence

ORD record
ord-03136747e36249b5a7566df7a338584e
Source dataset
uspto-grants-2000_04
Patent number
US06054414

Reaction notes

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