Hydrochloric Acid → HCID 19009231, compound

HRID 1742440Notes

Reaction equation

HRID 1742440 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH2:11]([C:21]1[NH:22][CH:23]=[CH:24][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl.O.O.O.C([O-])(=O)C.[Na+]>ClCCCl.O>[CH2:11]([C:21]1[NH:22][C:23]([CH:3]=[O:4])=[CH:24][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19009232HCID 19009232, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 19009231HCID 19009231, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

To an ice cooled 4 g (56 mmol) of dimethylformamide was added 8.6 g (56 mmol) of phosphorous oxychloride over a period of 15 minutes while stirring under a nitrogen atmosphere. The mixture was stirred 15 minutes and then 15 mL of 1,2-dichloroethane was added. To this mixture was added a solution of 10.5 g (50.6 mmol) of 2-decylpyrrole, 35, in 15 mL of 1,2-dichloroethane while cooling in an ice bath. The reaction mixture was then heated under reflux for 15 minutes, during which time there was copious evolution of hydrogen chloride gas. After cooling to room temperature, a solution of sodium acetate trihydrate (38.1 g, 280 mmol) in 50 mL of water was added to the mixture. After heating at reflux for 15 minutes, the mixture was cooled and the 1,2-dichloroethane layer was separated. The aqueous layer was extracted with chloroform. The combined organic extracts were washed with saturated aqueous sodium carbonate solution and dried over anhydrous sodium carbonate. Following evaporation of solvent under vacuum, the crude product was purified by silica gel column chromatography with 1:9 ethyl acetate/hexanes as eluant, giving 9.8 g (82%) of compound 38 as a white solid.

Workup

  1. stirringThe mixture was stirred 15 minutes
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux for 15 minutes, during which time there
  4. temperatureAfter heating
  5. temperatureat reflux for 15 minutes
  6. temperaturethe mixture was cooled
  7. customthe 1,2-dichloroethane layer was separated
  8. extractionThe aqueous layer was extracted with chloroform
  9. washThe combined organic extracts were washed with saturated aqueous sodium carbonate solution
  10. dry with materialdried over anhydrous sodium carbonate
  11. customevaporation of solvent under vacuum
  12. customthe crude product was purified by silica gel column chromatography with 1:9 ethyl acetate/hexanes as eluant

Sources & evidence

ORD record
ord-63cc1eb038b14eadbe4ff54127cc47d5
Source dataset
uspto-grants-1994_08
Patent number
US05338854

Reaction notes

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