Pyridine → HCID 58610111, compound

HRID 1442571Notes

Reaction equation

HRID 1442571 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.[CH:17]1([C:21](Cl)=[O:22])[CH2:20][CH2:19][CH2:18]1>C(OC)(C)(C)C.O.Cl>[CH:17]1([C:21]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[O:22])[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 54432-Mercaptobenzoic AcidHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 58610111HCID 58610111, compoundYield 96.4%

Reagents, catalysts & solvents 3

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

Procedure

Thiosalicylic acid (6.17 g, 40 mmol) was suspended in tert-butylmethyl ether (100 ml) at room temperature. While stirring under ice cooling, pyridine (7.91 g, 100 mmol) and then cyclobutanecarbonyl chloride (5.00 g, 42 mmol) were dropwise added to the suspension. After the reaction mixture was stirred for 2 hours, the mixture was diluted with water and 6N hydrochloric acid was added thereto to make its liquid property acidic. The mixture was extracted (100 ml×3) with tert-butylmethyl ether-tetrahydrofuran (3:1, v/v). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by distillation to give the title compound (9.11 g, 96%). A part (1.0 g) of the compound was recrystallized from ethyl acetate-hexane to give colorless crystals (0.81 g).

Workup

  1. stirringAfter the reaction mixture was stirred for 2 hours
  2. additionwas added
  3. extractionThe mixture was extracted (100 ml×3) with tert-butylmethyl ether-tetrahydrofuran (3:1
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-fcce6759374947759dacd4e283d6a927
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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