Pyridine → HCID 178426104, compound

HRID 1442603Notes

Reaction equation

HRID 1442603 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.[S:12](Cl)(Cl)=O.[C:16]([OH:25])(=O)[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)S.N1C=CC=CC=1>C(Cl)(Cl)Cl.O.Cl.C(OC)(C)(C)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:23]2[CH:22]=[CH:21][CH:20]=[CH:18][C:17]=2[C:16]([OH:25])=[S:12])=[O:8])=[C:4]([CH3:11])[CH:3]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 54432-Mercaptobenzoic AcidHCID 24386Thionyl ChlorideHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 178426104HCID 178426104, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-Chloro-2-methylbenzoic acid (5.00 g, 29 mmol) was dissolved in chloroform (30 ml) and thionyl chloride (10 ml) was added to the solution. The mixture was heated under reflux overnight. The reaction solution was concentrated under reduced pressure. While stirring under ice cooling, the concentrate was dropwise added to a mixture of thiosalicylic acid (4.00 g, 26 mmol), pyridine (5.13 g, 65 mmol) and tert-butylmethyl ether (50 ml). After the reaction mixture was stirred at the same temperature for 3 hours, the mixture was diluted with water and 6N hydrochloric acid was added thereto to make its liquid property acidic. The crystals precipitated were taken by filtration, washed with water and dried to give 2-[(4-chloro-2-methylphenyl)carbonyl]thiobenzoic acid (5.73 g, 72%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. stirringAfter the reaction mixture was stirred at the same temperature for 3 hours
  5. additionwas added
  6. customThe crystals precipitated
  7. filtrationwere taken by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-956f69570717418988075eaeb29bbd52
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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