Oxalyl chloride → 1-Azatricyclo[6.4.1.04,13]trideca-2,4(13)-diene-11,12-dione

HRID 4931

반응식

HRID 4931 반응식
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[NH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[C:1]1(=[O:5])[N:7]2[C:13]3[CH:12]([CH2:17][CH2:16][CH2:15][C:14]=3[CH:9]=[CH:8]2)[CH2:11][CH2:10][C:2]1=[O:3]

참가 물질

4

반응물 2

HCID 65578Oxalyl chlorideHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

생성물 1

HCID 573500091-Azatricyclo[6.4.1.04,13]trideca-2,4(13)-diene-11,12-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of oxalic chloride (27.5 ml) in tetrahydrofuran (THF; 500 ml) which was subjected to refluxing with heating, was dropwise added a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (28.8 g) in THF (100 ml), which was thereafter subjected to stirring for 4 hours as such. After cooled, the solvent was distilled off and the residue was dissolved into carbon disulfide (600 ml), to which then only small portions of aluminium chloride (52.27 g) were added at room temperature with stirring and was further subjected to stirring for 4 hours. With removal of supernatant solution from the reaction mixture, ice-water was added to the residue, which was then extracted with chloroform. The organic layer was thoroughly washed with water, dried over anhydrous sodium sulfate and then the solvent thereof was distilled off.

후처리

  1. temperatureto refluxing
  2. temperaturewith heating
  3. temperatureAfter cooled
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved into carbon disulfide (600 ml), to which
  6. additiononly small portions of aluminium chloride (52.27 g) were added at room temperature
  7. stirringwith stirring
  8. stirringto stirring for 4 hours
  9. customWith removal of supernatant solution from the reaction mixture, ice-water
  10. additionwas added to the residue, which
  11. extractionwas then extracted with chloroform
  12. washThe organic layer was thoroughly washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent thereof was distilled off

출처 및 근거

ORD 기록
ord-032ed9a94ceb4a87a0bff96b9f0cbbf6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242912

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