Pyridine → 2-{[4-(Acetylamino)benzoyl]thio}benzoic acid

HRID 1442574Notes

Reaction equation

HRID 1442574 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.[C:17]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)(=[O:19])[CH3:18]>O1CCCC1.O.Cl>[C:17]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[O:26])=[CH:23][CH:22]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 3

HCID 1049PyridineHCID 54432-Mercaptobenzoic AcidHCID 70103414-Acetamidobenzoyl chloride

Product 1

HCID 586101152-{[4-(Acetylamino)benzoyl]thio}benzoic acidYield 53%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Thiosalicylic acid (1.28 g, 8.3 mmol) was suspended in tetrahydrofuran (10 ml). While stirring, pyridine (1.64 g, 21 mmol) and then a tetrahydrofuran solution (5 ml) of 4-(acetylamino)benzoyl chloride (1.67 g, 9.1 mmol) were dropwise added to the suspension under ice cooling. 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 and the residue was recrystallized from ethyl acetate-isopropyl ether to give the title compound (1.38 g, 53%).

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 ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-726e6e77f399480d8a4e2481fb8a7d59
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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