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

HRID 1441086Notes

Reaction equation

HRID 1441086 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4'-chloro-2'-fluoro-5'-hydroxyphenyl)-3-(trifluoromethyl)glutarimide (1.64 g, 5.05 retool, 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.).

Workup

  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

Sources & evidence

ORD record
ord-ad75a070229b4b90bae667d38510625d
Source dataset
uspto-grants-1996_03
Patent number
US05502027

Reaction notes

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