Hydrochloric Acid → HCID 19009231, 화합물

HRID 1742440노트

반응식

HRID 1742440 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 19009231HCID 19009231, 화합물수율 82.3%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63cc1eb038b14eadbe4ff54127cc47d5
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338854

반응 노트

불러오는 중…