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

HRID 275429

反応式

HRID 275429 の反応式
[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

参加物

7

反応物 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 70726GlutarimideHCID 15767072N-(4'-chloro-2'-fluoro-5'-hydroxyphenyl)-3-(trifluoromethyl)glutarimide2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-7c28fb228d664c3b89d96d1292f1ea9d
出典データセット
uspto-grants-1995_02
特許番号
US05393735

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