Chloroform → N-[(+/-)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]-5-methylisoxazolidine

HRID 543581노트

반응식

HRID 543581 반응식
Cl.[CH3:2][CH:3]1[O:7][NH:6][CH2:5][CH2:4]1.C(Cl)(Cl)Cl.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:32]=[CH:31][C:24]([O:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])=[CH:23][CH:22]=2)=[N:18][CH:19]=1.C(N(CC)CC)C>O>[F:33][C:13]([F:12])([F:34])[C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:32]=[CH:31][C:24]([O:25][CH:26]([CH3:30])[C:27]([N:6]3[CH2:5][CH2:4][CH:3]([CH3:2])[O:7]3)=[O:28])=[CH:23][CH:22]=2)=[N:18][CH:19]=1

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 130552202-(4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoyl chlorideHCID 204600925-Methylisoxazolidine hydrochloride

생성물 1

HCID 13314624N-[(+/-)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]-5-methylisoxazolidine수율 95.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 5-methylisoxazolidine hydrochloride (13.6 g) and chloroform (200 ml), under stirring and ice-cooling, was added (±)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl chloride (34.6 g) and then added dropwise triethylamine (22.2 g). After the completion of addition, the reaction mixture was stirred for further 30 minutes at room temperature, to which water was added to form two layers. The organic layer so separated was washed with 1 N hydrochloric acid and then with 1 N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate. Removal of the solvent by a distillation in vacuo gave N-[(±)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl]-5-methylisoxazolidine (38.0 g) as a white crystalline solid which showed the melting point of 94°-97° C. after recrystallization from a mixture of n-hexane/acetone.

후처리

  1. temperatureice-cooling
  2. additionAfter the completion of addition
  3. additionwas added
  4. customto form two layers
  5. customThe organic layer so separated
  6. washwas washed with 1 N hydrochloric acid
  7. dry with materialwith 1 N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. distillationby a distillation in vacuo

출처 및 근거

ORD 기록
ord-a3dc27a546b442db9516d66ae8ae89db
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04447259

반응 노트

불러오는 중…