Pyridine → HCID 58610107, compound

HRID 1442575Notes

Reaction equation

HRID 1442575 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].N1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>O1CCCC1.O.Cl>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:22]

Participants

7

Reactant 3

HCID 1049PyridineHCID 54432-Mercaptobenzoic AcidHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 58610107HCID 58610107, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Thiosalicylic acid (1.38 g, 9.0 mmol) was suspended in tetrahydrofuran (10 ml). While stirring under ice cooling, pyridine (1.77 g, 22 mmol) and then a tetrahydrofuran solution (5 ml) of 2-methoxybenzoyl chloride (1.68 g, 9.9 mmol) were dropwise added to the suspension. After the reaction mixture was stirred for 15 hours, the mixture was diluted with water and 6N hydrochloric acid was added thereto to make its liquid property acidic. The mixture was extracted (50 ml×2) with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was recrystallized from tetrahydrofuran-isopropyl ether to give the title compound (2.08 g, 73%).

Workup

  1. stirringAfter the reaction mixture was stirred for 15 hours
  2. additionwas added
  3. extractionThe mixture was extracted (50 ml×2) with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customThe residue was recrystallized from tetrahydrofuran-isopropyl ether

Sources & evidence

ORD record
ord-20c50053f8b147cda75d0c118471d1df
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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