Pyridine → HCID 59609086, compound

HRID 1183869Notes

Reaction equation

HRID 1183869 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.N1C=CC=CC=1.[Cl:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>CC(C)=O>[O:16]=[C:5]1[C:4]2[CH:3]=[C:2]([O:1][C:26](=[O:27])[CH2:25][CH2:24][Cl:23])[CH:15]=[CH:14][C:13]=2[S:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 693643-Chloropropionyl chlorideHCID 97945682-Hydroxy-9H-thioxanthen-9-one

Product 1

HCID 59609086HCID 59609086, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g (22 mmol) of 2-hydroxy-9H-thioxanthen-9-one was dissolved in 200 ml refluxing acetone. 3.6 ml (3.5 g, 44 mmol) pyridine was added, followed by the addition of 5.6 g (44 mmol) 3-chloropropionyl chloride. The mixture was refluxed for 5 hours. The solvent was removed under reduced pressure, after cooling down to room temperature and the residue was dissolved in 200 ml methylene chloride. The methylene chloride was extracted with 150 ml of a 1 M Na2CO3 solution and 150 ml of a 0.1 N hydrochloric acid solution. The organic fraction was dried over MgSO4 and evaporated under reduced pressure. 3-chloro-propionic acid 9-oxo-9H-thioxanthen-2-yl ester was isolated by preparative column chromatography on a SVP D40 Merck NP column, using a gradient elution from methylene chloride (20 minutes isocratic elution) to methylene chloride/ethyl acetate 80/20 over 30 minutes and a flow rate of 50 ml/min. 0.414 g of 3-chloro-propionic acid 9-oxo-9H-thioxanthen-2-yl ester (6%) was isolated as a white crystalline compound.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 200 ml methylene chloride
  4. extractionThe methylene chloride was extracted with 150 ml of a 1 M Na2CO3 solution and 150 ml of a 0.1 N hydrochloric acid solution
  5. dry with materialThe organic fraction was dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f49a98fc55174b0ebb396b6a522eac9c
Source dataset
uspto-grants-2014_03
Patent number
US08664431B2

Reaction notes

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