Triethylamine → 2-(2,6-Dinitrophenyl)ethoxycarbonyl chloride

HRID 963750노트

반응식

HRID 963750 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2].CCN(CC)CC.[Cl:23][C:24](OC(Cl)(Cl)Cl)=[O:25]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][O:15][C:24]([Cl:23])=[O:25])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 108675832-(2,6-Dinitrophenyl)ethanol

생성물 1

HCID 190827052-(2,6-Dinitrophenyl)ethoxycarbonyl chloride수율 97.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-(2,6-dinitrophenyl)ethanol (4.08 g, 19.23 mmol) and Et3N (2.7 ml, 19.28 mmol) in THF (30 ml, dist. over CaH2) was dropped in a solution, cooled to 0° C., of trichloromethyl chloroformate (3.81 g, 2.33 ml, 19.28 mmol) in THF (10 ml, see above) for 20 min. This solution was stirred for 25 min while cooling in an ice bath, and was then stirred for 1 h 45 min at room temperature. The mixture was filtered over Celite. Rewashing the filter cake with THF, removing the solvent and excess reagent from the pooled filtrates by distillation and drying in a high vacuum yielded 5.13 g 2-(2,6-dinitrophenyl)-ethoxycarbonyl chloride (97%) as a light-brown solid.

후처리

  1. temperaturewhile cooling in an ice bath
  2. stirringwas then stirred for 1 h 45 min at room temperature
  3. filtrationThe mixture was filtered over Celite
  4. customremoving the solvent and excess reagent from the pooled filtrates
  5. distillationby distillation
  6. customdrying in a high vacuum

출처 및 근거

ORD 기록
ord-791c3164c9eb486b8a01e2622374f8fc
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763599

반응 노트

불러오는 중…