Triethylamine → HCID 58610089, compound

HRID 1442583Notes

Reaction equation

HRID 1442583 reaction equation
[CH:1]1([C:4]([S:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9](O)=[O:10])=O)[CH2:3][CH2:2]1.C([N:18](CC)CC)C.ClC(OCC)=O.[N-]=[N+]=[N-].[Na+].C(P(CCCC)CCCC)CCC>CC(C)=O.O.C1(C)C=CC=CC=1>[CH:1]1([C:4]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=[O:10])[N:18]=2)[CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13831TributylphosphineHCID 33557Sodium AzideHCID 86603549HCID 86603549, compound

Product 1

HCID 58610089HCID 58610089, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-15 °C

Procedure

2-[(Cyclopropylcarbonyl)thio]benzoic acid (11.11 g, 50 mmol) was suspended in acetone (150 ml). While stirring under ice cooling, triethylamine (5.10 g, 50 mmol) and then ethyl chloroformate (6.68 g, 62 mmol) were dropwise added to the suspension. After stirring at the same temperature for an hour, an aqueous solution (15 ml) of sodium azide (5.00 g, 77 mmol) was dropwise added to the reaction mixture and stirring was continued for further an hour. The reaction mixture was diluted with water and the dilution was extracted with toluene (100 ml×3). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and then filtered. The toluene solution was cooled to about −15° C. and a solution (10 ml) of tributylphosphine (10.50 g, 52 mmol) in toluene was dropwise added to the solution. After completion of the dropwise addition, the reaction temperature was reverted to room temperature and the mixture was heated under reflux for 15 minutes. The reaction solution was concentrated under reduced pressure. The residue was applied to column chromatography using silica gel (300 g) to elute with hexane-ethyl acetate (2:1, v/v). The eluate was recrystallized from ethyl acetate-hexane to give the title compound (2.85 g, 28%) as crystals.

Workup

  1. stirringAfter stirring at the same temperature for an hour
  2. stirringstirring
  3. waitwas continued for further an hour
  4. extractionthe dilution was extracted with toluene (100 ml×3)
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. additionAfter completion of the dropwise addition
  9. customwas reverted to room temperature
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for 15 minutes
  12. concentrationThe reaction solution was concentrated under reduced pressure
  13. washto elute with hexane-ethyl acetate (2:1, v/v)
  14. customThe eluate was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-11921602a3f945bcab209669a2c444b4
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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