Pyridine → N-(4'-chloro-2'-fluoro-5'-(benzenesulphonyloxy)phenyl)-3-(trifluoromethyl)glutarimide

HRID 275429

반응식

HRID 275429 반응식
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([F:19])([F:18])[F:17])[CH2:11][C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.N1C=CC=CC=1.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(=O)NC(=O)CCC1>C(Cl)Cl.O>[Cl:1][C:2]1[C:7]([O:8][S:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:36])=[O:35])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([F:18])([F:17])[F:19])[CH2:11][C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 70726GlutarimideHCID 15767072N-(4'-chloro-2'-fluoro-5'-hydroxyphenyl)-3-(trifluoromethyl)glutarimide2회

생성물 1

HCID 15767071N-(4'-chloro-2'-fluoro-5'-(benzenesulphonyloxy)phenyl)-3-(trifluoromethyl)glutarimide수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(4'-chloro-2'-fluoro-5'-hydroxyphenyl)-3-(trifluoromethyl)glutarimide (1.64 g, 5.05 mmol, Compound 19) in about 20 ml of methylene chloride was added via syringe nearly 2.5 eq. of pyridine (1 ml) which had been freshly distilled from CaH2. Then a solution of benzenesulfonyl chloride (0.64 ml, 5.0 mmol) in 4.5 ml of methylene chloride was slowly added dropwise to the reaction mixture with ice bath cooling. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Then there was added 0.17 g of additional glutarimide and the reaction mixture was stirred at room temperature for an additional 12 hours. The reaction mixture was poured into 50 ml of water and the layers were separated. The organic layer was evaporated in vacuo and the residue was dried in the vacuum oven (20-50 Torr, 50° C.). The resulting brown solid was rinsed with approximately 5 ml of methylene chloride and suction filtered to yield 1.9 g (82% yield) of the desired product as an off-white powder (m.p. 214°-215° C.).

후처리

  1. distillationhad been freshly distilled from CaH2
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred at room temperature for an additional 12 hours
  4. customthe layers were separated
  5. customThe organic layer was evaporated in vacuo
  6. customthe residue was dried in the vacuum oven (20-50 Torr, 50° C.)
  7. washThe resulting brown solid was rinsed with approximately 5 ml of methylene chloride and suction
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-7c28fb228d664c3b89d96d1292f1ea9d
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393735

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