Pyridine → HCID 58610098, compound

HRID 1442576Notes

Reaction equation

HRID 1442576 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]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18](C(Cl)=O)=[CH:19][CH:20]=[CH:21][CH:22]=1.[O:32]1CCC[CH2:33]1>O.Cl>[C:26]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:27]=[CH:28][C:29]([C:33]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[O:32])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 54432-Mercaptobenzoic AcidHCID 8028Tetrahydrofuran2×HCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 58610098HCID 58610098, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Thiosalicylic acid (1.06 g, 6.9 mmol) was suspended in tetrahydrofuran (10 ml). While stirring under ice cooling, pyridine (1.36 g, 17 mmol) and then a tetrahydrofuran solution (5 ml) of 1,1′-biphenylcarbonyl chloride (1.64 g, 7.6 mmol) were dropwise added to the suspension. After the reaction mixture was stirred for 14 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-tetrahydrofuran (3:1, v/v). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, followed by distillation to remove the solvent. The residue was recrystallized from ethyl acetate to give the title compound (1.29 g, 56%).

Workup

  1. stirringAfter the reaction mixture was stirred for 14 hours
  2. additionwas added
  3. extractionThe mixture was extracted (50 ml×2) with ethyl acetate-tetrahydrofuran (3:1
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationfollowed by distillation
  7. customto remove the solvent
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0a5f63bbe0fb4223bf3614f62009c241
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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